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

HRID 1095164Notes

Reaction equation

HRID 1095164 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].C([O-])([O-])=O.[K+].[K+].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][O:6][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 22479327Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoateYield 52.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (13.2 g, 0.1 mol), K2CO3 (20 g, 0.14 mol) and DMAP (6.2 g, 0.05 mol) in DCM (100 mL) was added p-toluenesulfonyl chloride (19 g, 0.1 mol). The mixture was stirred at room temperature overnight, then filtered. The filtrate was washed with HCl aq. (1 M) and water, dried over anhydrous Na2SO4 and concentrated to give the title compound (15 g).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with HCl aq. (1 M) and water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-95e9a5a2bed941b89a180778f71142e9
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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