1-(Triphenylphosphoranylidene)acetone → HCID 21538222, compound

Participants

Reaction Steps

A mixture of 6 parts of 1,4-diacetoxy-2,3-dimethoxy-6-formyl-5-methylbenzene, 12 parts of 2-oxo-1-propylidenetriphenylphosphoran and 500 volume parts of dioxane is stirred under reflux for 17 hours and the reaction mixture is evaporated to dryness. The residue is purified by chromatography on a column of silica gel, whereupon 1,4-diacetoxy-2,3-dimethoxy-5-methyl-6-(3'-oxo-1'-butenyl)-benzene (Formula (VII) wherein R=OCH3 ; OY, OY'=OCOCH3) is obtained as a brown oil. 2 Parts of this product is reacted with 2.77 parts of 2-propargyloxytetrahydropyran, reduced catalytically and hydrolyzed in the same manner as Reference Example 4. The described procedure gives 1,4-diacetoxy-2,3-dimethoxy-5-methyl-6-(6'-hydroxy-3'-methylhexyl)benzene (Formula (IX) wherein R=OCH3 ; OY, OY'=OCOCH3 ; OY"=OH) as a colourless oil.

Provenance & Evidence