Water → 3-Hydroxybutyl 4-methylbenzenesulfonate

HRID 2216433Notes

Reaction equation

HRID 2216433 reaction equation
N1C=CC=CC=1.[CH2:7]([OH:12])[CH2:8][CH:9]([OH:11])[CH3:10].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>C(Cl)Cl>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:12][CH2:7][CH2:8][CH:9]([CH3:10])[OH:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 78961,3-Butanediol

Product 1

HCID 132043233-Hydroxybutyl 4-methylbenzenesulfonateYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (9.0 ml, 111 mmol) was added to a solution of 1,3-butanediol (5.07 g, 56.3 mmol) in anhydrous methylene chloride (20 ml) at room temperature. After ice-cooling, p-toluenesulfonyl chloride (15.9 g, 83.4 mmol) was added thereto, the mixture was stirred at room temperature overnight, then water (60 ml) was added to the reaction mixture, and the whole was extracted with ethyl acetate (100 ml). The ethyl acetate layer was washed with 1 N hydrochloric acid (30 ml) and saturated brine (30 ml) successively and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=3/1) to give 7.72 g (57%) of the target compound.

Workup

  1. temperatureAfter ice-cooling
  2. extractionthe whole was extracted with ethyl acetate (100 ml)
  3. washThe ethyl acetate layer was washed with 1 N hydrochloric acid (30 ml) and saturated brine (30 ml) successively
  4. customEthyl acetate was evaporated under reduced pressure
  5. customthe obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-0b8b9a7073104ff087d29a212d73e988
Source dataset
uspto-grants-2006_09
Patent number
US07112598B2

Reaction notes

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