2-Bromoethanol → 2-(Phenylsulfonyl)ethanol

HRID 2350819Notes

Reaction equation

HRID 2350819 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]=1

Participants

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

  1. temperaturewas heated to 80°-90° C.
  2. temperaturewhile maintaining the pH of the reaction solution at 7-8
  3. additionAfter the addition
  4. stirringthe reaction solution was further stirred for 2 hours at 80°-90° C.
  5. extractionThen, the reaction solution was extracted with ethyl acetate
  6. concentrationThe ethyl acetate was concentrated
  7. 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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