Hydrogen Peroxide → HCID 10241262, compound

Participants

Reaction Conditions

Reaction Steps

To the dimethyl acetal of citronellal prepared in (a) is added 50 ml. of a 1M solution of diborane in tetrahydrofuran while the temperature of the reaction mixture is maintained at -10° to 0° .C. The reaction mixture is stirred at 0°C for 45 minutes and then at 20°C for 30 minutes. To this mixture is added 12.0 g. sodium hydroxide, as a 50% aqueous solution. Hydrogen peroxide (as a 30% aqueous solution) is added dropwise until residual peroxide is present. Heat evolved during this addition is dissipated by permitting the solvent to distill under reflux. The reaction mixture is shaken with hexane, the hexane layer is separated and washed in turn with 5% aqueous sodium sulfite solution and saturated brine. Solvent is removed from the solution under reduced pressure and the residue is distilled to yield the dimethyl acetal of 3,7-dimethyl-6-hydroxyoctan-1-al.

Provenance & Evidence