Potassium Hydroxide → Oxacycloheptadec-8-en-2-one, (8Z)-

HRID 1817Notes

Reaction equation

[CH2:1]([CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5]O.[OH-].[K+]>>[CH2:1]1[CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[O:19][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 5282940Ambrettolic acid

Product 1

HCID 5365703Oxacycloheptadec-8-en-2-one, (8Z)-

Conditions

Temperature: 180 °C

Procedure

Alternatively, the ester may be saponified to obtain the ambrettolic acid. The crude ambrettolic acid obtained by saponification was transformed into its glycerine polyester by heating under a slight vacuum at 180° C. for a period of 4 to 5 hours. The resulting polyesters were then depolymerized in the presence of a mineral base, potassium hydroxide, to give ambrettolide which was distilled off by azeotropic distillation using glycerine. After fractionation, 43 g of cis-oxacyclopheptadec-12-en-2-one (Product II) containing 86% of the cis-derivative and 13% of the trans-derivative, was obtained (as determined by GLC analysis) (Tb 125° C.-128° C. at 0.2 mm Hg).

Sources & evidence

ORD record: ord-8a2792e0ff14486c99220c32eed53e32
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726328

Reaction notes

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