Trifluoroacetic acid → 4-Carboxymethoxy-3-methyl-benzoic Acid Methyl Ester

HRID 220847Notes

Reaction equation

HRID 220847 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:27])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[C:13]([CH3:26])[CH:12]=1>ClCCl>[CH3:8][O:9][C:10](=[O:27])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[C:13]([CH3:26])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 575554074-tert-Butoxycarbonylmethoxy-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575553254-Carboxymethoxy-3-methyl-benzoic Acid Methyl EsterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 ml) was added to a solution of 4-tert-butoxycarbonylmethoxy-3-methyl-benzoic acid methyl ester from Example E41.1 (3.8 g, 13.6 mmol) in di-chloromethane (40 ml) and the mixture was stirred for 1 h at room temperature. Volatiles were removed in vacuo and azeotroped with dichloromethane to yield the title compound (3.04 g, 100%).

Workup

  1. customVolatiles were removed in vacuo
  2. customazeotroped with dichloromethane

Sources & evidence

ORD record
ord-213e6bd1296e41729536b74672aab7b8
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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