Trifluoroacetic acid → 4-(4-Methoxycarbonyl-butyl)-3-methyl-benzoic Acid

HRID 220827Notes

Reaction equation

HRID 220827 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:29])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:16]([CH3:28])[CH:15]=1)(C)(C)C>ClCCl>[CH3:27][O:26][C:24]([CH2:23][CH2:22][CH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([OH:29])=[O:12])=[CH:15][C:16]=1[CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 575553334-(4-Methoxycarbonyl-butyl)-3-methyl-benzoic Acid Tert-butyl Ester

Product 1

HCID 575553514-(4-Methoxycarbonyl-butyl)-3-methyl-benzoic AcidYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 ml) was added to a solution of 4-(4-methoxycarbonyl-butyl)-3-methyl-benzoic acid tert-butyl ester from Example E31.3 (1.43 g, 4.7 mmol) in di-chloromethane (40 ml) and the mixture was stirred for 2 h at room temperature. Solvents were concentrated in vacuo and azeotroped with dichloromethane to yield the title compound (1.07 g, 92%).

Workup

  1. concentrationSolvents were concentrated in vacuo
  2. customazeotroped with dichloromethane

Sources & evidence

ORD record
ord-ee9f03a88a234524b626194affa8090b
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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