Trifluoroacetic acid → 3-Methyl-4-phenoxybenzoic acid

HRID 1501035Notes

Reaction equation

HRID 1501035 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7]C(C)(C)C)=[O:6].FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89581022Tert-butyl 3-methyl-4-phenoxybenzoate

Product 1

HCID 206460583-Methyl-4-phenoxybenzoic acidYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of tert-butyl 3-methyl-4-phenoxybenzoate (654 mg, 2.3 mmol), 2,2,2-trifluoroacetic acid (1 mL) and dichloromethane (4 mL) were stirred at 20° C. for 4 hours. The mixture was washed with water (10 mL×2). The organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give 3-methyl-4-phenoxybenzoic acid as a white solid (200 mg, 38%). LRMS (M+H)− m/z: calcd 228.08. found 228.

Workup

  1. washThe mixture was washed with water (10 mL×2)
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e654d2879caa499590f796fbabc79d49
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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