Trifluoroacetic acid → 4-(Carboxymethoxy)-benzoic acid 1-methyl ester

HRID 1292749Notes

Reaction equation

HRID 1292749 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])=[CH:6][CH:5]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60482321Methyl 4-(2-tert-butoxy-2-oxoethoxy)benzoate

Product 1

HCID 138161514-(Carboxymethoxy)-benzoic acid 1-methyl esterYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-tert-butoxycarbonylmethoxy-benzoic acid methyl ester (5 g, 18.8 mmol) in dry DCM (40 ml) is added trifluoro-acetic acid (40 ml) at 0° C. The solution is stirred for 5 h at rt and evaporated in vacuo to give 4-carboxymethoxy-benzoic acid methyl ester 4 g as a white solid. LC-MS2: tR=3.24 min, [M+1]+=211.04, [M−1]−=208.96.

Workup

  1. customevaporated in vacuo

Sources & evidence

ORD record
ord-906399b61508463c9beb9bc5116a9c63
Source dataset
uspto-grants-2007_07
Patent number
US07238685B2

Reaction notes

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