4-tert-butyl-2,6-bis(hydroxymethyl)phenol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 200 grams (1.331 moles) of para-t-butylphenol and 400 ml. of water were placed in a 2-liter, 3-neck, round bottom flask fitted with a thermometer, a stirrer and a dropping funnel. The flask was placed in a water bath, the contents stirred and 106.6 grams (1.331 moles) of 50% aq. NaOH added. The temperature of the resulting slurry was adjusted to 30° C. (by cooling) and 227 grams (~2.8 moles) of 37% formalin added. The mixture was heated to 60° C. and stirred at that temperature for 4 hours. It was then cooled to 35° C. and 444 ml. (1.331 moles) of 3 N aq. HCl were added. Enough dilute acetic acid was then added to make the mixture just acid. 100 ml. of chloroform was stirred in and the phases allowed to separate. The chloroform layer, containing essentially all of the product resin, was removed, washed once with water, dried by azeotropic distillation and stripped in vacuo. 276 grams (99% yield) of the title product was obtained as a resinous residue which crystallized on standing; equivalent wt. 220 grams per phenolic --OH (vs 212, theoretical). fitted with a thermometer, a stirrer and a dropping funnel The flask was placed in a water bath was adjusted to 30° C. added stirred at that temperature for 4 hours It was then cooled to 35° C. to separate The chloroform layer, containing essentially all of the product resin was removed washed once with water dried by azeotropic distillation

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 200 grams (1.331 moles) of para-t-butylphenol and 400 ml. of water were placed in a 2-liter, 3-neck, round bottom flask fitted with a thermometer, a stirrer and a dropping funnel. The flask was placed in a water bath, the contents stirred and 106.6 grams (1.331 moles) of 50% aq. NaOH added. The temperature of the resulting slurry was adjusted to 30° C. (by cooling) and 227 grams (~2.8 moles) of 37% formalin added. The mixture was heated to 60° C. and stirred at that temperature for 4 hours. It was then cooled to 35° C. and 444 ml. (1.331 moles) of 3 N aq. HCl were added. Enough dilute acetic acid was then added to make the mixture just acid. 100 ml. of chloroform was stirred in and the phases allowed to separate. The chloroform layer, containing essentially all of the product resin, was removed, washed once with water, dried by azeotropic distillation and stripped in vacuo. 276 grams (99% yield) of the title product was obtained as a resinous residue which crystallized on standing; equivalent wt. 220 grams per phenolic --OH (vs 212, theoretical). fitted with a thermometer, a stirrer and a dropping funnel The flask was placed in a water bath was adjusted to 30° C. added stirred at that temperature for 4 hours It was then cooled to 35° C. to separate The chloroform layer, containing essentially all of the product resin was removed washed once with water dried by azeotropic distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2, 6-di(hydroxymethyl) phenol. dissolved the solution was stirred for four to six days at ambient temperature A yellow, oily organic phase was isolated washed with three 500 ml portions of water Chloroform (700 ml) and 500 ml of water were added to this organic oil the mixture was stirred The organic phase was isolated dried over 100 g of anhydrous magnesium sulphate Evaporation cooling of the chloroform solution yielded a mixture of white crystals and oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2, 6-di(hydroxymethyl) phenol. dissolved the solution was stirred for four to six days at ambient temperature A yellow, oily organic phase was isolated washed with three 500 ml portions of water Chloroform (700 ml) and 500 ml of water were added to this organic oil the mixture was stirred The organic phase was isolated dried over 100 g of anhydrous magnesium sulphate Evaporation cooling of the chloroform solution yielded a mixture of white crystals and oil

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 200 grams (1.331 moles) of para-t-butylphenol and 400 ml. of water were placed in a 2-liter, 3-neck, round bottom flask fitted with a thermometer, a stirrer and a dropping funnel. The flask was placed in a water bath, the contents stirred and 106.6 grams (1.331 moles) of 50% aq. NaOH added. The temperature of the resulting slurry was adjusted to 30° C. (by cooling) and 227 grams (~2.8 moles) of 37% formalin added. The mixture was heated to 60° C. and stirred at that temperature for 4 hours. It was then cooled to 35° C. and 444 ml. (1.331 moles) of 3 N aq. HCl were added. Enough dilute acetic acid was then added to make the mixture just acid. 100 ml. of chloroform was stirred in and the phases allowed to separate. The chloroform layer, containing essentially all of the product resin, was removed, washed once with water, dried by azeotropic distillation and stripped in vacuo. 276 grams (99% yield) of the title product was obtained as a resinous residue which crystallized on standing; equivalent wt. 220 grams per phenolic --OH (vs 212, theoretical). fitted with a thermometer, a stirrer and a dropping funnel The flask was placed in a water bath was adjusted to 30° C. added stirred at that temperature for 4 hours It was then cooled to 35° C. to separate The chloroform layer, containing essentially all of the product resin was removed washed once with water dried by azeotropic distillation

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 200 grams (1.331 moles) of para-t-butylphenol and 400 ml. of water were placed in a 2-liter, 3-neck, round bottom flask fitted with a thermometer, a stirrer and a dropping funnel. The flask was placed in a water bath, the contents stirred and 106.6 grams (1.331 moles) of 50% aq. NaOH added. The temperature of the resulting slurry was adjusted to 30° C. (by cooling) and 227 grams (~2.8 moles) of 37% formalin added. The mixture was heated to 60° C. and stirred at that temperature for 4 hours. It was then cooled to 35° C. and 444 ml. (1.331 moles) of 3 N aq. HCl were added. Enough dilute acetic acid was then added to make the mixture just acid. 100 ml. of chloroform was stirred in and the phases allowed to separate. The chloroform layer, containing essentially all of the product resin, was removed, washed once with water, dried by azeotropic distillation and stripped in vacuo. 276 grams (99% yield) of the title product was obtained as a resinous residue which crystallized on standing; equivalent wt. 220 grams per phenolic --OH (vs 212, theoretical). fitted with a thermometer, a stirrer and a dropping funnel The flask was placed in a water bath was adjusted to 30° C. added stirred at that temperature for 4 hours It was then cooled to 35° C. to separate The chloroform layer, containing essentially all of the product resin was removed washed once with water dried by azeotropic distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2,6-di(hydroxymethyl)phenol. dissolved the solution was stirred for four to six days at ambient temperature A yellow, oily organic phase was isolated washed with three 500 ml portions of water Chloroform (700 ml) and 500 ml of water were added to this organic oil the mixture was stirred The organic phase was isolated dried over 100 g of anhydrous magnesium sulphate Evaporation cooling of the chloroform solution yielded a mixture of white crystals and oil

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 200 grams (1.331 moles) of para-t-butylphenol and 400 ml. of water were placed in a 2-liter, 3-neck, round bottom flask fitted with a thermometer, a stirrer and a dropping funnel. The flask was placed in a water bath, the contents stirred and 106.6 grams (1.331 moles) of 50% aq. NaOH added. The temperature of the resulting slurry was adjusted to 30° C. (by cooling) and 227 grams (~2.8 moles) of 37% formalin added. The mixture was heated to 60° C. and stirred at that temperature for 4 hours. It was then cooled to 35° C. and 444 ml. (1.331 moles) of 3 N aq. HCl were added. Enough dilute acetic acid was then added to make the mixture just acid. 100 ml. of chloroform was stirred in and the phases allowed to separate. The chloroform layer, containing essentially all of the product resin, was removed, washed once with water, dried by azeotropic distillation and stripped in vacuo. 276 grams (99% yield) of the title product was obtained as a resinous residue which crystallized on standing; equivalent wt. 220 grams per phenolic --OH (vs 212, theoretical). fitted with a thermometer, a stirrer and a dropping funnel The flask was placed in a water bath was adjusted to 30° C. added stirred at that temperature for 4 hours It was then cooled to 35° C. to separate The chloroform layer, containing essentially all of the product resin was removed washed once with water dried by azeotropic distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2,6-di(hydroxymethyl)phenol. dissolved the solution was stirred for four to six days at ambient temperature A yellow, oily organic phase was isolated washed with three 500 ml portions of water Chloroform (700 ml) and 500 ml of water were added to this organic oil the mixture was stirred The organic phase was isolated dried over 100 g of anhydrous magnesium sulphate Evaporation cooling of the chloroform solution yielded a mixture of white crystals and oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37%) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2,6-di(hydroxymethyl) phenol. dissolved the solution was stirred for four to six days at ambient temperature A yellow, oily organic phase was isolated washed with three 500 ml portions of water Chloroform (700 ml) and 500 ml of water were added to this organic oil the mixture was stirred The organic phase was isolated dried over 100 g of anhydrous magnesium sulphate Evaporation cooling of the chloroform solution yielded a mixture of white crystals and oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system formed. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2,6-di(hydroxymethyl) phenol. dissolved the solution was stirred for four to six days at ambient temperature formed A yellow, oily organic phase was isolated washed with three 500 ml portions of water Chloroform (700 ml) and 500 ml of water were added to this organic oil the mixture was stirred The organic phase was isolated dried over 100 g of anhydrous magnesium sulphate Evaporation cooling of the chloroform solution yielded a mixture of white crystals and oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2,6-di(hydroxymethyl)phenol. dissolved the solution was stirred for four to six days at ambient temperature A yellow, oily organic phase was isolated washed with three 500 ml portions of water Chloroform (700 ml) and 500 ml of water were added to this organic oil the mixture was stirred The organic phase was isolated dried over 100 g of anhydrous magnesium sulphate Evaporation cooling of the chloroform solution yielded a mixture of white crystals and oil