(3-甲基-2H-1,4-苯并二恶英-3-基)甲醇

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture (23.7 g) of 2-hydroxymethyl-2-methyl-1,4-benzodioxan and 3-hydroxy-3-methyl-2H-1,5-benzodioxepine (~3:1 ratio; prepared according to the method of A. Salimbeni, E. Manghisi, J. Heterocyclic Chem., 17, 489, 1980) was stirred with 1 N aqueous sodium hydroxide solution (135 ml) and cooled to 0°-10°. A solution of potassium permanganate (42 g) in water (165 ml) was added slowly so that the temperature was maintained below 10°. After 48 hours at room temperature the mixture was filtered and the filtrate acidified with 1 M aqueous sulphuric acid and extracted with methylene chloride. The extracts were washed with aqueous sodium bicarbonate solution and the aqueous layer was acidified with sulphuric acid. Extraction with methylene chloride followed by washing, drying and evaporation of the extracts gave the carboxylic acid (11.5 g); m.p. 125°-129.5°. prepared cooled to 0°-10° was maintained below 10° After 48 hours at room temperature the mixture was filtered extracted with methylene chloride The extracts were washed with aqueous sodium bicarbonate solution Extraction with methylene chloride by washing drying evaporation of the extracts

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Jones' reagent (33.3 ml.) was added dropwise to a stirred solution of 2-hydroxymethyl-2-methyl-1,4-benzodioxan (5 g.) in acetone (300 ml.) at 5° C., then the reaction was allowed to attain room temperature. Isopropanol (10 ml.) was then added followed by water (200 ml.), the solution extracted with chloroform and the extracts evaporated in vacuo. The residual oil was taken up in chloroform (200 ml.) then extracted with dilute sodium bicarbonate solution and the aqueous phase further washed with chloroform. The aqueous phase was then acidified with hydrochloric acid, extracted with chloroform, the combined extracts washed with water, dried (MgSO4) and evaporated in vacuo ti give 2-methyl-1,4-benzodioxan-2-carboxylic acid (1.7 g.). A sample was recrystallized from toluene, m.p. 133°-134° C. to attain room temperature the solution extracted with chloroform the extracts evaporated in vacuo then extracted with dilute sodium bicarbonate solution the aqueous phase further washed with chloroform extracted with chloroform the combined extracts washed with water dried (MgSO4) evaporated in vacuo ti

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture (23.7 g) of 2-hydroxymethyl-2-methyl-1,4-benzodioxan and 3-hydroxy-3-methyl-2H-1,5-benzodioxepine (~3:1 ratio; prepared according to the method of A. Salimbeni, E. Manghisi, J. Heterocyclic Chem., 17, 489, 1980) was stirred with 1 N aqueous sodium hydroxide solution (135 ml) and cooled to 0°-10°. A solution of potassium permanganate (42 g) in water (165 ml) was added slowly so that the temperature was maintained below 10°. After 48 hours at room temperature the mixture was filtered and the filtrate acidified with 1 M aqueous sulphuric acid and extracted with methylene chloride. The extracts were washed with aqueous sodium bicarbonate solution and the aqueous layer was acidified with sulphuric acid. Extraction with methylene chloride followed by washing, drying and evaporation of the extracts gave the carboxylic acid (11.5 g); m.p. 125°-129.5°. prepared cooled to 0°-10° was maintained below 10° After 48 hours at room temperature the mixture was filtered extracted with methylene chloride The extracts were washed with aqueous sodium bicarbonate solution Extraction with methylene chloride by washing drying evaporation of the extracts