Trifluoroacetic acid → 7-Phenylhept-2-enoic acid

HRID 1107105Notes

Reaction equation

HRID 1107105 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][C:13]([O:15]C(C)(C)C)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54541139t-Butyl 7-phenyl-2-heptenoate

Product 1

HCID 543401997-Phenylhept-2-enoic acidYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-butyl 7-phenylhept-2-enoate (19 g; 70 mmol) is dissolved in dry CH2Cl2 (120 mL) and trifluoroacetic acid (25 mL) is added slowly. After 5 hours the reaction is concentrated in vacuo and purified by column chromatography using CH2Cl2 to obtain 7-phenylhept-2-enoic acid (7 g; 34 mmol). 1H NMR (300 MHz, CDCl3) δ 12-10 (br, 1H), 7.30-7.24 (m, 2H), 7.20-7.12 (m, 3H), 7.06 (dd, J=15.7, 7 Hz, 1H), 5.80 (d, J=15.7 Hz, 1H), 2.62 (t, J=7.5 HZ, 2H), 2.25 (q, J=7 HZ, 2H), 1.70-1.61 (m, 2H), 1.56-1.46 (m, 2H).

Workup

  1. concentrationAfter 5 hours the reaction is concentrated in vacuo
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-e136eb3b0b31488cbd29f8e22e564c39
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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