2-Bromoethanol → 2-(Phenylsulfonyl)ethanol
Reaction equation
[C:1]1([S:7]([O-:10])(=[O:9])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[CH2:12](Br)[CH2:13][OH:14].[OH-].[Na+]>>[C:1]1([S:7]([CH2:12][CH2:13][OH:14])(=[O:9])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
4
Procedure
1,000 ml of an aqueous solution containing 509 g (2.16 mol) of sodium benzenesulfonate (dihydrate) was heated to 80°-90° C. and stirred. To this solution were added at the same time 539 g (4.31 mol) of ethylenebromohydrin and 100 ml of an aqueous solution containing 45 g of sodium hydroxide while maintaining the pH of the reaction solution at 7-8. After the addition was completed, the reaction solution was further stirred for 2 hours at 80°-90° C. and then cooled to room temperature. Then, the reaction solution was extracted with ethyl acetate. The ethyl acetate was concentrated and distilled off under reduced pressure to yield 113 g of the desired product having a boiling point of 172 to 174° C./0.4 mmHg.
Workup
- temperaturewas heated to 80°-90° C.
- temperaturewhile maintaining the pH of the reaction solution at 7-8
- additionAfter the addition
- stirringthe reaction solution was further stirred for 2 hours at 80°-90° C.
- extractionThen, the reaction solution was extracted with ethyl acetate
- concentrationThe ethyl acetate was concentrated
- distillationdistilled off under reduced pressure
Sources & evidence
- ORD record
- ord-26aded66af2b4aee8e3157ca3b82bbb1
- Source dataset
- uspto-grants-1989_10
- Patent number
- USH0000691
Reaction notes
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