2,6,6-trimethylcyclohex-2-ene-1-carbaldehyde

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: 9.3 Ml of a 1.42N slution of butyl-lithium in hexane (0.0132M) were added dropwise at -78° to a solution of 2.0 g (0.011M) of methyl alpha-cyclogeranate in 40 ml of anhydrous tetrahydrofuran (THF). Once the addition was over, the temperature of the mixture was increased to +15° and, at this temperature, 3.17 ml (0.011M) of a 70% solution of VITRIDE [sodium bis(2-methoxyethoxy)aluminum hydride] in toluene were added thereto. The reaction mixture was heated to 40° for 45 mn, then hydrolyzed by pouring it onto an icy saturated aqueous solution of ammonium chloride. The mixture was extracted with ether, the organic phase was separated and then subjected to the usual treatments of neutralization and washing to give a residue which, upon distillation, gave 1.27 g of alpha-cyclocitral having b.p. 60°-65°/66 Pa (purity: 80%; yield: 65%). Once the addition were added The reaction mixture was heated to 40° for 45 mn The mixture was extracted with ether the organic phase was separated washing to give a residue which upon distillation

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

Procedure: Allyl chloride (5 ml.) was added under nitrogen to a suspension of magnesium (28.8 g.) in 300 ml. of dry ether. According to the usual procedure of a Grignard reaction, allyl chloride (85 g.) and α-cyclocitral (152 g.) in 100 ml. of dry ether were added at such a rate as to maintain the solvent at reflux. At this temperature, the mixture was left during 3 h. and poured then into an NH4Cl aqueous solution. to maintain the solvent at reflux poured

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