2-(2-hydroxypropan-2-yl)phenol

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

Procedure: A solution of 10.0 ml (11.31 g, 83.1 mmol) of 2′-hydroxyacetophenone and 50 ml of tetrahydrofuran was placed in an ice bath and treated with 120.0 ml (168.0 mmol) of 1.4M methyllithium in tetrahydrofuran, which was added dropwise over 30 minutes. The reaction mixture first became cloudy and then cleared up. After stirring for 18 hours, the solution was acidified with 4% aqueous hydrochloric acid. The layers were separated. The organic phase was washed with 30 ml of brine, dried over sodium sulfate, and concentrated. A total of 12.05 g of 2-(dimethylhydroxymethyl)phenol was isolated. was added dropwise over 30 minutes The layers were separated The organic phase was washed with 30 ml of brine dried over sodium sulfate concentrated

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

Procedure: A solution of 10.0 ml (11.31 g, 83.1 mmol) of 2′-hydroxyacetophenone and 50 ml of tetrahydrofuran was placed in an ice bath and treated with 120.0 ml (168.0 mmol) of 1.4M methyllithium in tetrahydrofuran, which was added dropwise over 30 minutes. The reaction mixture first became cloudy and then cleared up. After stirring for 18 hours, the solution was acidified with 4% aqueous hydrochloric acid. The layers were separated. The organic phase was washed with 30 ml of brine, dried over sodium sulfate, and concentrated. A total of 12.05 g of 2-(dimethylhydroxymethyl)phenol was isolated. was added dropwise over 30 minutes The layers were separated The organic phase was washed with 30 ml of brine dried over sodium sulfate concentrated

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of epoxide 30 (10.0 g, 32.57 mmol) in DMF (30 ml) was added alcohol 31 (7.425 g, 48.85 mmol), potassium carbonate (8.99 g, 65.14 mmol). The reaction mixture was stirred overnight at 120-130° C. The resulted mixture was treated with 10% aq. acetic acid, diluted further with water followed by usual workup in ethyl acetate and FC to give diol 32 (7.0 g, 46%).

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

Procedure: To a stirred solution of methyl magnesium chloride (134 ml, 3M in THF) kept under nitrogen, at 0° C. was added a solution of 2-hydroxy acetophenone (50 g, 367 mmol) in anhydrous THF (100 ml). The reaction mixture was stirred. After completion of the reaction, the reaction mixture was treated with 4M acetic acid (500 ml) followed by usual workup in dichloromethane and FC to give hydroxy phenol 31 (25 g, 45%) as a colorless oil. kept under nitrogen, at 0° C. After completion of the reaction

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

Procedure: To a stirred solution of methyl magnesium chloride (134 ml, 3M in THF) kept under nitrogen, at 0° C. was added a solution of 2-hydroxy acetophenone (50 g, 367 mmol) in anhydrous THF (100 ml). The reaction mixture was stirred. After completion of the reaction, the reaction mixture was treated with 4M acetic acid (500 ml) followed by usual workup in dichloromethane and FC to give hydroxy phenol 31 (25 g, 45%) as a colorless oil. kept under nitrogen, at 0° C. After completion of the reaction

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

Procedure: A solution of 10.0 ml (11.31 g, 83.1 mmol) of 2′-hydroxyacetophenone and 50 ml of tetrahydrofuran was placed in an ice bath and treated with 120.0 ml (168.0 mmol) of 1.4M methyllithium in tetrahydrofuran, which was added dropwise over 30 minutes. The reaction mixture first became cloudy and then cleared up. After stirring for 18 hours, the solution was acidified with 4% aqueous hydrochloric acid. The layers were separated. The organic phase was washed with 30 ml of brine, dried over sodium sulfate, and concentrated. A total of 12.05 g of 2-(dimethylhydroxymethyl)phenol was isolated. was added dropwise over 30 minutes The layers were separated The organic phase was washed with 30 ml of brine dried over sodium sulfate concentrated

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

Procedure: A solution of 10.0 ml (11.31 g, 83.1 mmol) of 2′-hydroxyacetophenone and 50 ml of tetrahydrofuran was placed in an ice bath and treated with 120.0 ml (168.0 mmol) of 1.4 M methyllithium in tetrahydrofuran, which was added dropwise over 30 minutes. The reaction mixture first became cloudy and then cleared up. After stirring for 18 hours, the solution was acidified with 4% aqueous hydrochloric acid. The layers were separated. The organic phase was washed with 30 ml of brine, dried over sodium sulfate, and concentrated. A total of 12.05 g of 2-(dimethylhydroxymethyl)phenol was isolated. was added dropwise over 30 minutes The layers were separated The organic phase was washed with 30 ml of brine dried over sodium sulfate concentrated

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

Procedure: A solution of 10.0 ml (11.31 g, 83.1 mmol) of 2′-hydroxyacetophenone and 50 ml of tetrahydrofuran was placed in an ice bath and treated with 120.0 ml (168.0 mmol) of 1.4M methyllithium in tetrahydrofuran, which was added dropwise over 30 minutes. The reaction mixture first became cloudy and then cleared up. After stirring for 18 hours, the solution was acidified with 4% aqueous hydrochloric acid. The layers were separated. The organic phase was washed with 30 ml of brine, dried over sodium sulfate, and concentrated. A total of 12.05 g of 2-(dimethylhydroxymethyl)phenol was isolated. was added dropwise over 30 minutes The layers were separated The organic phase was washed with 30 ml of brine dried over sodium sulfate concentrated

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of epoxide 30 (10.0 g, 32.57 mmol) in DMF (30 ml) was added alcohol 31 (7.425 g, 48.85 mmol), potassium carbonate (8.99 g, 65.14 mmol). The reaction mixture was stirred overnight at 120-130° C. The resulted mixture was treated with 10% aq. acetic acid, diluted further with water followed by usual workup in ethyl acetate and FC to give diol 32 (7.0 g, 46%).

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

Procedure: To a stirred solution of methyl magnesium chloride (134 ml, 3M in THF) kept under nitrogen, at 0° C. was added a solution of 2-hydroxy acetophenone (50 g, 367 mmol) in anhydrous THF (100 ml). The reaction mixture was stirred. After completion of the reaction, the reaction mixture was treated with 4M acetic acid (500 ml) followed by usual workup in dichloromethane and FC to give hydroxy phenol 31 (25 g, 45%) as a colorless oil. kept under nitrogen, at 0° C. After completion of the reaction