Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 178501516, compound

HRID 67047

Reaction equation

HRID 67047 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:24][CH3:25])(=[O:23])[C@@H:19]([CH2:21][OH:22])[OH:20]>COC(OC)(C)C>[CH2-:18][C:19]([CH3:21])=[O:20].[C:18]([O:24][CH3:25])(=[O:23])[C@@H:19]([CH2:21][OH:22])[OH:20]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 9920382(R)-Methyl 2,3-dihydroxypropanoate

Product 1

HCID 178501516HCID 178501516, compoundYield 161.2%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

Pyridinium p-toluenesulfonate (50 mg) was added to a solution of 8.3 g of (R)-methyl glycerate in 30 ml of 2,2-dimethoxypropane and the mixture was refluxed for 30 minutes. The reaction mixture was purified by columnchromatography using silica gel (120 g) and hexane:ethyl acetate (5:1) as an eluant to give 9.87 g (89%) of (R)-methyl glycerate acetonide.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. customThe reaction mixture was purified by columnchromatography

Sources & evidence

ORD record
ord-be803e2e7a2542ef86a45fe266a84ce0
Source dataset
uspto-grants-1982_08
Patent number
US04344888

Linked notes

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