4-Toluenesulfonyl chloride → Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoate

HRID 1728177Notes

Reaction equation

HRID 1728177 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][O:6][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:10])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 22479327Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoateYield 89.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (13.2 g, 100 mmol), 4-methyl-benzenesulfonyl chloride (18.1 g, 90 mmol), 4-dimethylamino pyridine (15.9 g, 130 mmol) in dichloromethane was stirred at room temperature for 1 h. Then the mixture was washed by aqueous HCl solution (1 N), brine and dried over Na2SO4. The solvent was removed in vacuum to give title compound (23 g).

Workup

  1. washThen the mixture was washed by aqueous HCl solution (1 N), brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-8a9fb65362c043f8a422d6536bbe2bbc
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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