Ethyl Acetate → p-Toluenesulfonic acid

HRID 2108207Notes

Reaction equation

HRID 2108207 reaction equation
C(OCC)(=O)C.O.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1>>[C:8]1([CH3:18])[CH:9]=[CH:10][C:11]([S:14]([OH:17])(=[O:15])=[O:16])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acid

Procedure

A compound of Formula (IV) wherein the protecting group R5 is a trityl group is dissolved in a reaction-inert solvent (e.g., ethyl acetate), 1.0 to 1.5 molar equivalents of p-toluenesulfonic acid monohydrate is added under ice-cooling, and then the mixture is stirred for 1 to 5 hours to give the compound of Formula (V) in the form of p-toluenesulfonic acid salt. If necessary, the p-toluenesulfonic acid salt is treated with a base to give the compound of Formula (V) in the form of the free base.

Workup

  1. additionis added under ice-
  2. temperaturecooling

Sources & evidence

ORD record
ord-8dca6c4e66b14bbfb7a0d1008ba3b126
Source dataset
uspto-grants-1990_06
Patent number
US04937332

Reaction notes

Loading…