Trifluoroacetic acid → 2-Methyl-4-(1-phenylethyl)benzoic acid

HRID 1501200Notes

Reaction equation

HRID 1501200 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:14]=[C:13]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89581013Tert-butyl 2-methyl-4-(1-phenylethyl)benzoate

Product 1

HCID 895814372-Methyl-4-(1-phenylethyl)benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-methyl-4-(1-phenylethyl)benzoate (1.6 g, 5.4 mmol) in dichloromethane 9 mL, and 3 mL trifluoroacetic acid was added. The mixture was stirred 0.5 hour. Thin layer chromatography showed full conversion. The reaction mixture was concentrated to give 2-methyl-4-(1-phenylethyl)benzoic acid (1 g, 90%).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-2bac5739529f421fbe22be87e77d5b43
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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