Water → HCID 20469262, compound

Participants

Reaction Conditions

Reaction Steps

Reaction: ##STR31## To a solution of methyl 1-(3-methyl-2-butenyl)-2-oxo-4-isopropoxy-6-methyl-3-cyclohexene carboxylate (29.4 g, 0.1 mol) in anhydrous hexamethylphosphoric triamide (220 mL) was added anhydrous lithium chloride (6.4 g, 0.15 mol). The mixture was stirred at 130° C. in a nitrogen atmosphere for 1.5 hours and then added to water (800 mL). The aqueous solution was extracted with ether. The combined ether extracts were washed with water and dried (Na2SO4). The ether was removed on a rotary evaporator and the residue vacuum distilled, yielding 20.1 g of 3-isopropoxy-5-methyl-6-(3-methyl-2-butenyl)-2-cyclohexen-1-one, bp 104°-108° C./0.05 mm. The product was shown by glc/ms to be a mixture of "cis" and "trans" isomers in a ratio of 76:24.

Provenance & Evidence