ChemicalBook CAS DataBase List 6-Heptenoic acid

6-Heptenoic acid synthesis

9synthesis methods

Product Name:6-Heptenoic acid
CAS Number:1119-60-4
Molecular formula:C7H12O2
Molecular Weight:128.17

synthesis of 6-Heptenoic acid and higher homologs of this ω-unsaturated acid, a study of the pyrolysis of wheptano lactone was undertaken. The lactone was prepared by the oxidation of cycloheptanone under Baeyer-Villiger conditions. The pyrolysis of ω-unsaturated acid was effected by dropping the substance under a nitrogen atmosphere into a heated column packed with glass beads.
Synthesis of 6-Heptenoic Acid

25118-23-4 Synthesis

25118-23-4
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$27.00/250mg

1119-60-4
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$39.00/250mg

Yield:1119-60-4 91.8%

Reaction Conditions:

Stage #1:ethyl 6-heptenoate with sodium hydroxide in ethanol;water for 4 h;Reflux;
Stage #2: with hydrogenchloride in water; pH=5

Steps:

1 Hept-6-enoic acid (52a):
Hept-6-enoic acid (52a):To a stirred solution of Ethyl hept-6-enoate (52) (3 g, 19.2 mmol) in EtOH (100 mL), IN NaOH (7.6 g, 192.3 mmol) was added and refluxed for 4 h. The volatiles from the reaction were removed under reduced pressure, the residue was acidified (pH 5) with IN HC1 and extracted with CH₂CI₂ (3 x 25 mL). The combined organic extracts were dried over anhydrous Na₂S0₄, filtered and concentrated under reduced pressure to afford compound 52a (2.26 g, 91.8%) as colorless liquid.TLC: 20% EtOAc/Hexane (R_f: 0.1)1H NMR (500MHz, CDC1₃): δ 5.83-5.75 (m, 1H), 5.06 (dd, 7 = 17, 1.5 Hz, 2H), 2.39 (t, J = 7.5 Hz, 2H), 2.09-2.04 (m, 2H), 1.66-1.60 (m, 2H), 1.47-1.43 (m, 2H).Mass (ESI): 127 (M⁺-l).

References:

THERACRINE, INC.;SUN, Lijun;BARSOUM, James;WESTER, Ronald WO2013/13240, 2013, A2 Location in patent:Page/Page column 58

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64-19-7 Synthesis