Trifluoroacetic acid → [3-(Methoxycarbonyl)phenoxy]acetic acid

HRID 1524262Notes

Reaction equation

HRID 1524262 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH:5]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid3×HCID 16094634Methyl 3-(2-(tert-butoxy)-2-oxoethoxy)benzoate

Product 1

HCID 13816150[3-(Methoxycarbonyl)phenoxy]acetic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-tert-butoxycarbonylmethoxy-benzoic acid methyl ester (1.00 g, 3.75 mmol) in methylene chloride (4 mL), add trifluoroacetic acid (0.50 mL, 6.6 mmol). Stir the mixture overnight at room temperature in an open vial to allow the solvent to escape. Add an additional portion of trifluoroacetic acid (0.50 mL, 6.6 mmol) and stir the reaction mixture for an additional 24 hours. Add an additional portion of trifluoroacetic acid (1.50 mL, 19.8 mmol) and stir the reaction at room temperature for 3 days. Concentrate under reduced pressure to provide 0.750 g (95.0%) of 3-carboxymethoxy-benzoic acid methyl ester as a light brown solid.

Workup

  1. stirringstir the reaction mixture for an additional 24 hours
  2. stirringstir
  3. customthe reaction at room temperature for 3 days
  4. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-8610483fc47d4313861198ccbf83b3c0
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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