2-[(2-tert-butylphenoxy)methyl]oxirane

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

Procedure: A mixture of 16.7 parts of ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, 14.7 parts of 3-(2-t-butylphenoxy)-1,2 -epoxypropane, 50 parts of dimethyl formamide, and 0.1 parts of benzyltrimethyl ammonium hydroxide was boiled under reflux for 3 hours, evaporated to leave a dark brown oil, and treated with ethyl acetate, which was then washed with 2% sodium hydroxide solution, and water, dried, and evaporated to an oil. The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which was boiled with an aqueous ethanolic solution of sodium bicarbonate. The mixture was acidified to give a solid, which was recrystallised from ethanol after treatment with charcoal to give 4.6 parts of 8-(3-[2-t-butylphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid as a cream solid, mp. 227°-228° (decomp.). under reflux for 3 hours evaporated to leave a dark brown oil was then washed with 2% sodium hydroxide solution, and water dried evaporated to an oil The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which to give a solid, which was recrystallised from ethanol after treatment with charcoal

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

Procedure: A mixture of 16.7 parts of ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, 14.7 parts of 3-(2-t-butylphenoxy)-1,2 -epoxypropane, 50 parts of dimethyl formamide, and 0.1 parts of benzyltrimethyl ammonium hydroxide was boiled under reflux for 3 hours, evaporated to leave a dark brown oil, and treated with ethyl acetate, which was then washed with 2% sodium hydroxide solution, and water, dried, and evaporated to an oil. The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which was boiled with an aqueous ethanolic solution of sodium bicarbonate. The mixture was acidified to give a solid, which was recrystallised from ethanol after treatment with charcoal to give 4.6 parts of 8-(3-[2-t-butylphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid as a cream solid, mp. 227°-228° (decomp.). under reflux for 3 hours evaporated to leave a dark brown oil was then washed with 2% sodium hydroxide solution, and water dried evaporated to an oil The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which to give a solid, which was recrystallised from ethanol after treatment with charcoal

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

Procedure: To a solution of 40 parts of o-t-butylphenol, 75 parts of epichlorhydrin, and 40 parts of ethanol boiling under reflux with stirring was added dropwise over 10 minutes a solution of 17.6 parts of potassium hydroxide dissolved in 66 parts of ethanol and the minimum amount of water. The mixture was stirred and refluxed for 105 minutes, cooled, diluted with water, and well extracted with ether, which was then washed with water, dried over magnesium sulphate, and evaporated to an oil. Distillation at 144° /8 mm afforded 43 parts of 3-(2-t-butylphenoxy)-1,2-epoxypropane as a clear oil. The mixture was stirred refluxed for 105 minutes cooled well extracted with ether, which was then washed with water dried over magnesium sulphate evaporated to an oil Distillation at 144° /8 mm

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

Procedure: A mixture of 16.7 parts of ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, 14.7 parts of 3-(2-t-butylphenoxy)-1,2-epoxypropane 50 parts of dimethyl formamide, and 0.1 parts of benzyltrimethyl ammonium hydroxide was boiled under reflux for 3 hours, evaporated to leave a dark brown oil, and treated with ethyl acetate, which was then washed with 2% sodium hydroxide solution, and water, dried, and evaporated to an oil. The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which was boiled with an aqueous ethanolic solution of sodium bicarbonate. The mixture was acidified to give a solid, which was recrystallised from ethanol after treatment with charcoal to give 4.6 parts of 8-(3-[2-t-butylphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid as a cream solid, mp. 227-228 (decomp.). under reflux for 3 hours evaporated to leave a dark brown oil was then washed with 2% sodium hydroxide solution, and water dried evaporated to an oil The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which to give a solid, which was recrystallised from ethanol after treatment with charcoal

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

Procedure: To a solution of 40 parts of o-t-butylphenol, 75 parts of epichlorhydrin, and 40 parts of ethanol boiling under reflux with stirring was added dropwise over 10 minutes a solution of 17.6 parts of potassium hydroxide dissolved in 66 parts of ethanol and the minimum amount of water. The mixture was stirred and refluxed for 105 minutes, cooled, diluted with water, and well extracted with ether, which was then washed with water, dried over magnesium sulphate, and evaporated to an oil. Distillation at 144°/8 mm afforded 43 parts of 3-(2-t-butylphenoxy)-1,2-epoxypropane as a clear oil. The mixture was stirred refluxed for 105 minutes cooled well extracted with ether, which was then washed with water dried over magnesium sulphate evaporated to an oil Distillation at 144°/8 mm

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

Procedure: A mixture of 16.7 parts of ethyl 8-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, 14.7 parts of 3-(2-t-butylphenoxy)-1,2 -epoxypropane, 50 parts of dimethyl formamide, and 0.1 parts of benzyltrimethyl ammonium hydroxide was boiled under reflux for 3 hours, evaporated to leave a dark brown oil, and treated with ethyl acetate, which was then washed with 2% sodium hydroxide solution, and water, dried, and evaporated to an oil. The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which was boiled with an aqueous ethanolic solution of sodium bicarbonate. The mixture was acidified to give a solid, which was recrystallised from ethanol after treatment with charcoal to give 4.6 parts of 8-(3-[2-t-butylphenoxy]-2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid as a cream solid, mp. 227°-228° (decomp.). under reflux for 3 hours evaporated to leave a dark brown oil was then washed with 2% sodium hydroxide solution, and water dried evaporated to an oil The oil was chromatographed on a silica column with chloroform as eluent to give a gummy solid, which to give a solid, which was recrystallised from ethanol after treatment with charcoal

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

Procedure: To a solution of 40 parts of o-t-butylphenol, 75 parts of epichlorhydrin, and 40 parts of ethanol boiling under reflux with stirring was added dropwise over 10 minutes a solution of 17.6 parts of potassium hydroxide dissolved in 66 parts of ethanol and the minimum amount of water. The mixture was stirred and refluxed for 105 minutes, cooled, diluted with water, and well extracted with ether, which was then washed with water, dried over magnesium sulphate, and evaporated to an oil. Distillation at 144° /8 mm afforded 43 parts of 3-(2-t-butylphenoxy)-1,2-epoxypropane as a clear oil. The mixture was stirred refluxed for 105 minutes cooled well extracted with ether, which was then washed with water dried over magnesium sulphate evaporated to an oil Distillation at 144° /8 mm