Hydrogen Peroxide → 4,4-Dimethyl-5-methoxypentan-1-ol

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Reaction Steps

Borane-methyl sulphide complex (2.76 ml., 2M solution in tetrahydrofuran, Aldrich) was added to 4,4-dimethyl-5-methoxypent-1-ene (1.9 g.) in dry hexane (50 ml.) under nitrogen at 0°. The mixture was stirred at 20° for 2 hours and ethanol (15 ml.) was added. 2N Aqueous sodium hydroxide solution (6.0 ml.) was then added. The mixture was cooled to 0° and hydrogen peroxide (5.3 ml., 30% aqueous solution) was added dropwise. The mixture was refluxed for 1 hour, cooled and poured into iced water (100 ml.). The aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and 4,4-dimethyl-5-methoxypentan-1-ol was obtained as a colourless oil (1.12 g).

Provenance & Evidence