Water → HCID 54103281, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 46.9 g (0.20 mole) of 4-acetoxybenzenesulfonyl chloride (I) in 400 ml dichloromethane contained in a 500-ml round-buttomed flask was dried over magnesium sulfate, then filtered and placed in a 3-liter, 3-necked, round-buttomed flask equipped with a stirrer, an additional funnel, a condenser and a thermometer. After subsequent cooling to 5° C., 142.2 g (0.70 mole) of diethanolamine (II) were added slowly with stirring. The reaction mixture was allowed to reach room temperature and was then stirred for 2 hours, followed by the addition of a mixture of 30 ml sodium hydroxide (50%) and 20 ml water. The resulting two phase mixture was stirred at room temperature for an additional two hours. The aqueous layer was extracted with two 150-ml portions of dichloromethane, and the aqueous phase was cooled in an ice bath and acidified with concentrated HCl to a pH of 2.0. Sodium hydroxide was added to saturate the aqueous phase, which was then extracted with ten 300-ml portions of ethylacetate, followed by roto-evaporation of the combined ethyl acetate extracts to dryness. A white solid (III) was collected, washed with heptane and dried under vacuum. The yield was 24.7 g (42.3%).

Provenance & Evidence