2-tert-butylbenzene-1,4-diol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Using 6.65 g of 2-tert-butyl-1,4-dihydroxybenzene, 4.6 ml of benzoyl chloride and 200 ml of pyridine, reaction and workup carried out as in Reference Example gave 9.35 g of 4-benzoyloxy-2-tert-butylphenol as white crystals, m.p. 120-121° C. Using. 9.35 g of the white crystals, 1,47 g of sodium hydride, 6.27 g of benzyl bromide and 40 ml of DMF, reaction and workup carried out as in Example 12 gave 6.07 g of yellow oil.

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

Procedure: Using 6.65 g of 2-tert-butyl-1,4-dihydroxybenzene, 4.6 ml of benzoyl chloride and 200 ml of pyridine, reaction and workup carried out as in Reference Example gave 9.35 g of 4-benzoyloxy-2-tert-butylphenol as white crystals, m.p. 120-121° C. Using. 9.35 g of the white crystals, 1,47 g of sodium hydride, 6.27 g of benzyl bromide and 40 ml of DMF, reaction and workup carried out as in Example 12 gave 6.07 g of yellow oil.

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

Procedure: A mixture of 67.6 g (0.02 mole) 1-(3',5'-dibromo-4'-acetoxyphenyl)ethanol, 0.35 g freshly melted and then finely pulverized potassium hydrogen sulfate, and 0.5 g t-butylhydroquinone are heated at 20 Torr to 170°-190° C. The resulting product is distilled off (under vacuum) at a temperature of 140° to 160° C. It is taken up in ether, the ether solution is washed with Na2CO3, dried, and concentrated under vacuum. The remaining product is distilled at 0.02 mbar; the boiling point is 116° C. The isolated product, which is a highly viscous oil or a white, waxy solid, has a melting point of approximately 75° C. The reaction yield is 27 g. The resulting product is distilled off (under vacuum) at a temperature of 140° to 160° C the ether solution is washed with Na2CO3 dried concentrated under vacuum The remaining product is distilled at 0.02 mbar The reaction yield is 27 g

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

Procedure: Then, after adding a mixture of 17.2 g of acrylic acid and 150 g of toluene to the reaction mixture obtained above together with 1.0 g of t-butylhydroquinone, the reaction was further carried out under refluxing with stirring for 4 hours. After cooling to room temperature, the reaction mixture obtained was reprecipitated from 2 liters of methanol and the solid thus precipitated was collected by filtration and dried under reduced pressure to obtain 135 g of Macromonomer MM-1 having a weight average molecular weight of 6.8×103. ##STR51## Then, after adding

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

Procedure: Then, after adding a mixture of 17.2 g of acrylic acid and 150 g of toluene to the reaction mixture obtained above together with 1.0 g of t-butylhydroquinone, the reaction was further carried out under refluxing with stirring for 4 hours. After cooling to room temperature, the reaction mixture obtained was reprecipitated from 2 liters of methanol and the solid thus precipitated was collected by filtration and dried under reduced pressure to obtain 135 g of Macromonomer MM-1 having a weight average molecular weight of 6.8×103. ##STR51## Then, after adding

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

Procedure: 33.2 g of tert.-butyl hydroquinone, 41.35 g of methyl bromoacetate and 37.3 g of potassium carbonate (anhydrous) are refluxed in 300 ml of acetone under nitrogen for 3 days. The solvent is removed under reduced pressure and 500 ml of ether are added. This ether solution is washed with water, dried with magnesium sulfate and evaporated. The residue is distilled in vacuo. The brown distillate obtained at 138°-140° under 10-3 mm Hg is purified by means of column chromatography. The methyl 2-(3-tert.-butyl-4-hydroxyphenoxy)-acetate thus obtained can be crystallised from hexane. Melting point: 87°-89°. The solvent is removed under reduced pressure and 500 ml of ether are added This ether solution is washed with water dried with magnesium sulfate evaporated The residue is distilled in vacuo The brown distillate obtained at 138°-140° under 10-3 mm Hg is purified by means of column chromatography

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

Procedure: 33.2 g of tert.-butyl hydroquinone, 41.35 g of methyl bromoacetate and 37.3 g of potassium carbonate (anhydrous) are refluxed in 300 ml of acetone under nitrogen for 3 days. The solvent is removed under reduced pressure and 500 ml of ether are added. This ether solution is washed with water, dried with magnesium sulfate and evaporated. The residue is distilled in vacuo. The brown distillate obtained at 138°-140° under 10-3 mm Hg is purified by means of column chromatography. The methyl 2-(3-tert.-butyl-4-hydroxyphenoxy)-acetate thus obtained can be crystallised from hexane. Melting point: 87°-89°. The solvent is removed under reduced pressure and 500 ml of ether are added This ether solution is washed with water dried with magnesium sulfate evaporated The residue is distilled in vacuo The brown distillate obtained at 138°-140° under 10-3 mm Hg is purified by means of column chromatography

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

Procedure: 30 g. of tert-butylhydroquinone (Eastman-Kodak) were dissolved in 200 ml. of anhydrous ether and 30 g. of anhydrous sodium sulfate were added. To this mixture was added 60 g. of silver oxide in small increments. An exothermic reaction ensued. After shaking for 20 minutes, the reaction mixture was filtered and the filtrate evaporated under the hood. Yellow crystals of tert-butyl-p-benzoquinone were obtained melting at 55° -60° C. To this mixture was added 60 g An exothermic reaction the reaction mixture was filtered the filtrate evaporated under the hood

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

Procedure: 30 g. of tert-butylhydroquinone (Eastman-Kodak) were dissolved in 200 ml. of anhydrous ether and 30 g. of anhydrous sodium sulfate were added. To this mixture was added 60 g. of silver oxide in small increments. An exothermic reaction ensued. After shaking for 20 minutes, the reaction mixture was filtered and the filtrate evaporated under the hood. Yellow crystals of tert-butyl-p-benzoquinone were obtained melting at 55° -60° C. To this mixture was added 60 g An exothermic reaction the reaction mixture was filtered the filtrate evaporated under the hood