3-Methyl-2-buten-1-OL → HCID 53836050, compound

Participants

Reaction Steps

To a solution of 1.04 g (5.00 mmol) of (2,4-dihydroxy-6-methylphenyl) (2-methylpropyl) ketone (47) in dry 1,4-dioxane (10.0 ml), under nitrogen atmosphere, added 710 mg (5.00 mmol, 1.00 equivalent) of boron trifluoride ether complex in dioxane (5.0 ml) at 10° C. with stirring. Then, added 861 mg (10.0 mmol, 2.00 equivalents) of 3-methyl-2-butenol in dioxane (5.0 ml) slowly, allowing to elevate to room temperature, and stirred for five hours. Added ether to the reaction mixture and washed the ether layer with saturated sodium hydrogen carbonate aqueous solution and saturated brine, and dried over sodium sulfate. By removal of the solvent, obtained orange-colored oily substance as a crude product. Column chromatographic separation on silica gel (65 g of Wako Gel C-300, eluted with hexane: ethyl acetate at varying ratios=19:1-7:3) gave, in the order of elution, 246 mg of {3,5-bis(3-methyl-2-butenyl)-2-hydroxy-6-methyl-4-(3-methyl-2-butenyloxy)phenyl}(2-methylpropyl) ketone (51) as a light yellow viscous oil and 95 mg of {2,4-dihydroxy-6-methyl-3-(3-methyl-2-butenyl)phenyl}(2-methylpropyl) ketone (49) as a light yellow fine needles.

Provenance & Evidence