(2,6,6-trimethylcyclohex-2-en-1-yl)methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 1.25 g NaBH4 in 50 ml. 95% ethanol cooled in an ice bath was added dropwise with stirring 5.0 g alpha-cyclocitral which had been prepared as described in Example 1. When the addition was complete, the ice bath was removed and water was added to dissolve any remaining solids. The reaction mixture was then stirred overnight at room temperature. The solvent was removed at reduced pressure and the residue taken up in ether, washed with 1 N acetic acid, dilute sodium bicarbonate and water. The ether extract was dried over sodium sulfate and concentrated to give 3.6 g alpha-cyclogeraniol as a colorless oil of 95% purity by gas chromatographic analysis. was added dropwise had been prepared When the addition the ice bath was removed water was added to dissolve any remaining solids The solvent was removed at reduced pressure washed with 1 N acetic acid, dilute sodium bicarbonate and water The ether extract was dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 1.25 g NaBH4 in 50 ml. 95% ethanol cooled in an ice bath was added dropwise with stirring 5.0 g alpha-cyclocitral which had been prepared as described in Example 1. When the addition was complete, the ice bath was removed and water was added to dissolve any remaining solids. The reaction mixture was then stirred overnight at room temperature. The solvent was removed at reduced pressure and the residue taken up in ether, washed with 1 N acetic acid, dilute sodium bicarbonate and water. The ether extract was dried over sodium sulfate and concentrated to give 3.6 g alpha-cyclogeraniol as a colorless oil of 95% purity by gas chromatographic analysis. was added dropwise had been prepared When the addition the ice bath was removed water was added to dissolve any remaining solids The solvent was removed at reduced pressure washed with 1 N acetic acid, dilute sodium bicarbonate and water The ether extract was dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 1.25 g NaBH4 in 50 ml. 95% ethanol cooled in an ice bath was added dropwise with stirring 5.0 g alpha-cyclocitral which had been prepared as described in Example 1. When the addition was complete, the ice bath was removed and water was added to dissolve any remaining solids. The reaction mixture was then stirred overnight at room temperature. The solvent was removed at reduced pressure and the residue taken up in ether, washed with 1 N acetic acid, dilute sodium bicarbonate and water. The ether extract was dried over sodium sulfate and concentrated to give 3.6 g alpha-cyclogeraniol as a colorless oil of 95% purity by gas chromatographic analysis. was added dropwise had been prepared When the addition the ice bath was removed water was added to dissolve any remaining solids The solvent was removed at reduced pressure washed with 1 N acetic acid, dilute sodium bicarbonate and water The ether extract was dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 1.25 g NaBH4 in 50 ml. 95% ethanol cooled in an ice bath was added dropwise with stirring 5.0 g alpha-cyclocitral which had been prepared as described in Example 1. When the addition was complete, the ice bath was removed and water was added to dissolve any remaining solids. The reaction mixture was then stirred overnight at room temperature. The solvent was removed at reduced pressure and the residue taken up in ether, washed with 1 N acetic acid, dilute sodium bicarbonate and water. The ether extract was dried over sodium sulfate and concentrated to give 3.6 g alpha-cyclogeraniol as a colorless oil of 95% purity by gas chromatographic analysis. was added dropwise had been prepared When the addition the ice bath was removed water was added to dissolve any remaining solids The solvent was removed at reduced pressure washed with 1 N acetic acid, dilute sodium bicarbonate and water The ether extract was dried over sodium sulfate concentrated