Trifluoroacetic acid → 4-Cyclopentylbenzoic acid

HRID 1501178Notes

Reaction equation

HRID 1501178 reaction equation
[CH:1]1([C:6]2[CH:18]=[CH:17][C:9]([C:10]([O:12]C(C)(C)C)=[O:11])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:17][CH:18]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89580875HCID 89580875, compound

Product 1

HCID 141636714-Cyclopentylbenzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-cyclopentylbenzoate (350 mg, 1.42 mmol) in dichloromethane (10 mL) was added 2,2,2-trifluoroacetic acid (2 mL). After stirring at room temperature for 0.5 hour, the mixture was concentrated to give 4-cyclopentylbenzoic acid (200 mg, 74%) as a white solid. LRMS (M+H+) m/z: calcd 190.10. found 190. 1H NMR (300 MHz, CD3OD): δ 12.78 (br, 1H), 7.86 (d, J=8.1 Hz, 2H), 7.37 (d, J=8.1 Hz, 2H), 3.10-3.01 (m, 1H), 2.05-2.01 (m, 2H), 1.78-1.65 (m, 6H).

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-b7abf839bd834965be712d8547b5f25a
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…