Hydrochloric Acid → Methyl 11-methoxy-7,11-dimethyl-3-oxo-6-dodecenoate

HRID 436879Notes

Reaction equation

[CH3:1][O:2][C:3]([CH3:16])([CH3:15])[CH2:4][CH2:5][CH2:6][C:7]([CH3:14])=[CH:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:12].[C:17](=O)([O-:20])[O:18][CH3:19].[H-].[Na+].Cl>CN(C)C=O>[CH3:1][O:2][C:3]([CH3:16])([CH3:15])[CH2:4][CH2:5][CH2:6][C:7]([CH3:14])=[CH:8][CH2:9][CH2:10][C:11](=[O:13])[CH2:12][C:17]([O:18][CH3:19])=[O:20]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 900 mg of the product from Step B, 1 ml of methyl carbonate and 15 ml of dimethylformamide was heated to 40° C. and 360 mg of sodium hydride in a 50% oil suspension were added thereto portion wise and the mixture was stirred for 6 hours at room temperature. The mixture was poured into an aqueous hydrochloric acid solution and was extracted with petroleum ether (b.p.= 40°-75° C.). The extracts were washed with water, dried over sodium sulfate and evaporated to dryness. The residue was chromatographed over silica and was eluted with a 7-3 petroleum ether-ethyl ether mixture to obtain 374 mg of methyl 11-methoxy-7,11-dimethyl-3-oxo-6-dodecenoate in the form of a colorless oil.

Workup

extractionwas extracted with petroleum ether (b.p.= 40°-75° C.)
washThe extracts were washed with water
dry with materialdried over sodium sulfate
customevaporated to dryness
customThe residue was chromatographed over silica
washwas eluted with a 7-3 petroleum ether-ethyl ether mixture

Sources & evidence

ORD record: ord-26cefb315ec441a08003a475254ec5a2
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04028386

Reaction notes

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