Hydrogen Peroxide → HCID 15260033, compound

Participants

Reaction Steps

Delta-Pyronene (27.2 g.) in 100 ml diglyme was stirred at 25° C. with 2.3 g. NaBH4, and a solution of 10.1 ml BF3 etherate in 16 ml diglyme was added thereto over a period of 30 minutes. After completion of the addition, the reaction mixture was stirred for 1 hour at 25° after which excess hydride was decomposed with 20 ml H2O. Sodium hydroxide (22 ml of 13% solution) then was added followed by the addition of 20 ml of 30% H2O2 over a 20-30 minute period. This mixture was stirred for 1 hour at 25°-30°. Workup of this mixture involved extraction with 150 ml ether and washing with 10% NaCl solution. Solvent removal under reduced pressure provided 30 g of crude product which was fractionated at 10 mm on a Nester-Faust spinning band column to give 6.7 g pure 1-methylene-2-hydroxymethyl-3,3-dimethylcyclohexane (gamma-cyclogeraniol) and 4.0 g of 90-95% pure 1-hydroxymethyl-2-methylene-3,3-dimethylcyclohexane.

Provenance & Evidence