methyl hydrogen sulfate

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:

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: A tetrahydrofuran (206 mL) solution of 4-bromoacetophenone (61.4 g) and methyl formate (27.8 g) was added dropwise to a tetrahydrofuran (125 mL) suspension of sodium methoxide (25 g) under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added dropwise to a methanol sulfate solution (prepared by adding sulfuric acid (45.4 g) dropwise to methanol (150 mL) under ice cooling) at room temperature, and the mixture was stirred for 2 days. The reaction mixture was added dropwise at −5° C. to a 1 mol/L aqueous sodium hydroxide solution (925 mL), and then a 5 mol/L sulfuric acid aqueous solution was added thereto at the same temperature until the pH was 8. After ethyl acetate (500 mL) and water (500 mL) were added thereto, a 5 mol/L sulfuric acid aqueous solution was added at −5° C. until the pH was 8. The organic layer was separated and the water layer was extracted with ethyl acetate. Together with the organic layer, the water layer was sequentially washed with a 1 mol/L sodium chloride solution and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure, thereby giving 80 g of a target compound as an oily product. prepared the mixture was stirred for 2 days The organic layer was separated the water layer was extracted with ethyl acetate Together with the organic layer, the water layer was sequentially washed with a 1 mol/L sodium chloride solution a saturated sodium chloride solution, dried over magnesium sulfate concentrated under reduced pressure

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

Procedure: A tetrahydrofuran (206 mL) solution of 4-bromoacetophenone (61.4 g) and methyl formate (27.8 g) was added dropwise to a tetrahydrofuran (125 mL) suspension of sodium methoxide (25 g) under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added dropwise to a methanol sulfate solution (prepared by adding sulfuric acid (45.4 g) dropwise to methanol (150 mL) under ice cooling) at room temperature, and the mixture was stirred for 2 days. The reaction mixture was added dropwise at −5° C. to a 1 mol/L aqueous sodium hydroxide solution (925 mL), and then a 5 mol/L sulfuric acid aqueous solution was added thereto at the same temperature until the pH was 8. After ethyl acetate (500 mL) and water (500 mL) were added thereto, a 5 mol/L sulfuric acid aqueous solution was added at −5° C. until the pH was 8. The organic layer was separated and the water layer was extracted with ethyl acetate. Together with the organic layer, the water layer was sequentially washed with a 1 mol/L sodium chloride solution and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure, thereby giving 80 g of a target compound as an oily product. prepared the mixture was stirred for 2 days The organic layer was separated the water layer was extracted with ethyl acetate Together with the organic layer, the water layer was sequentially washed with a 1 mol/L sodium chloride solution a saturated sodium chloride solution, dried over magnesium sulfate concentrated under reduced pressure

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

Procedure: A tetrahydrofuran (206 mL) solution of 4-bromoacetophenone (61.4 g) and methyl formate (27.8 g) was added dropwise to a tetrahydrofuran (125 mL) suspension of sodium methoxide (25 g) under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added dropwise to a methanol sulfate solution (prepared by adding sulfuric acid (45.4 g) dropwise to methanol (150 mL) under ice cooling) at room temperature, and the mixture was stirred for 2 days. The reaction mixture was added dropwise at −5° C. to a 1 mol/L aqueous sodium hydroxide solution (925 mL), and then a 5 mol/L sulfuric acid aqueous solution was added thereto at the same temperature until the pH was 8. After ethyl acetate (500 mL) and water (500 mL) were added thereto, a 5 mol/L sulfuric acid aqueous solution was added at −5° C. until the pH was 8. The organic layer was separated and the water layer was extracted with ethyl acetate. Together with the organic layer, the water layer was sequentially washed with a 1 mol/L sodium chloride solution and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure, thereby giving 80 g of a target compound as an oily product. prepared the mixture was stirred for 2 days The organic layer was separated the water layer was extracted with ethyl acetate Together with the organic layer, the water layer was sequentially washed with a 1 mol/L sodium chloride solution a saturated sodium chloride solution, dried over magnesium sulfate concentrated under reduced pressure

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

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

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