Trifluoroacetic acid → 2-(2-Allylcyclohexylidene)acetic acid

HRID 2275994

Reaction equation

HRID 2275994 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[CH:10][C:11]([O:13]C(C)(C)C)=[O:12])[CH:2]=[CH2:3].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[CH:10][C:11]([OH:13])=[O:12])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89650211Tert-butyl 2-(2-allylcyclohexylidene)acetate

Product 1

HCID 2785322-(2-Allylcyclohexylidene)acetic acidYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2-allylcyclohexylidene)acetate (1.00 g, 4.230 mmol) in dichloromethane (40 mL) at room temperature was added trifluoroacetic acid (0.688 mL, 8.883 mmol) and the solution was stirred at room temperature overnight. The solvent was then evaporated and excess of trifluoroacetic acid was removed by co-evaporation with toluene, giving 2-(2-allylcyclohexylidene)acetic acid (768 mg, 100%) as a colorless oil; 1H NMR (400 MHz, CDCl3) 5.59 (1H, m), 5.46 (1H, s), 4.82 (2H, m), 3.36 (1H, m), 2.19 (1H, m), 2.12 (2H, m), 1.93 (1H, m), 1.71 (1H, m), 1.61 (1H, m), 1.55 (1H, m), 1.47 (2H, m), 1.22 (1H, m).

Workup

  1. customThe solvent was then evaporated and excess of trifluoroacetic acid
  2. customwas removed by co-evaporation with toluene

Sources & evidence

ORD record
ord-bca6c53f4f0f4891990e6f5fce71df9e
Source dataset
uspto-grants-2015_09
Patent number
US09131688B2

Linked notes

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