4-Toluenesulfonyl chloride → HCID 16050326, compound

HRID 855965Notes

Reaction equation

HRID 855965 reaction equation
[Cl:1][CH2:2][C@H:3]([OH:7])[CH2:4][CH2:5][OH:6].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C(C)=CC=CC=1C>[Cl:1][CH2:2][C@H:3]([OH:7])[CH2:4][CH2:5][O:6][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 7021080(R)-4-CHLORO-1,3-BUTANEDIOL

Product 1

HCID 16050326HCID 16050326, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent2×

Procedure

Thus obtained (R)-4-chloro-1,3-butanediol (35.8 g, 0.287 mol) was dissolved in 2,6-lutidine (180 mL). After adding p-toluenesulfonyl chloride (54.8 g, 287 mol) under ice cooling, temperature of the mixture was raised to room temperature and the mixture was stirred for 15 hours. After the reaction, 2,6-lutidine was removed in vacuo. To the residue were added ethyl acetate (150 mL) and water (75 mL) and the mixture was separated by a separating funnel. The organic layer was washed with 2N hydrochloric acid (100 mL) and saturated brine (70 mL), and the solvent was removed in vacuo to give (R)-4-chloro-3-hydroxy-1-p-toluenesulfonyloxybutane (56.7 g, yield: 70.8%).

Workup

  1. customwas removed in vacuo
  2. additionTo the residue were added ethyl acetate (150 mL) and water (75 mL)
  3. customthe mixture was separated by a separating funnel
  4. washThe organic layer was washed with 2N hydrochloric acid (100 mL) and saturated brine (70 mL)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-441edb7a36dd423b9c871582d524b5e4
Source dataset
uspto-grants-2007_08
Patent number
US07262310B2

Reaction notes

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