Ethyl Acetate → p-Toluenesulfonic acid

HRID 1649857Notes

Reaction equation

HRID 1649857 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 R4 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-39ccea25f21c4bdfa5eaf0b6d1653466
Source dataset
uspto-grants-1990_05
Patent number
US04921953

Reaction notes

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