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

HRID 2275994

Reaktionsgleichung

Reaktionsgleichung von HRID 2275994
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 2785322-(2-Allylcyclohexylidene)acetic acidAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bca6c53f4f0f4891990e6f5fce71df9e
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09131688B2

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