Sodium Bicarbonate → 1-Hydroxy-5-methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene

Participants

Reaction Conditions

Reaction Steps

1.52 g (5 mmol) of 1,5-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene (I) was dissolved in 20 ml of methanol and the mixture was cooled to 0° C. To the mixture was then added 47.6 mg (0.25 mmol) of paratoluenesulfonic acid hydrate. After the mixture was stirred at 0° C. for 3 hours, a saturated aqueous sodium bicarbonate solution was added to the mixture and the resulting mixture was subjected to extraction with ether, followed by washing with a saturated brine. The resulting product was dried over anhydrous magnesium sulfate and the solvent was evaporated to obtain 1-hydroxy-5-methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene- 1-yl) -2,6,8-nonatriene (IV) as a mixture of E and Z isomers in a yield of 85%.

Provenance & Evidence