(6-methylcyclohex-3-en-1-yl)methanol

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction flask was charged with tetrahydrofuran (THF, 500 mL) and sodium amide (NaNH2, 100 g, 2.6 mol) and heated to reflux (˜65° C.). (6-Methyl-cyclohex-3-enyl)-methanol (300 g, 2.3 mol) was fed in. The reaction mixture was aged for a half-hour. Bromomethyl-cyclopropane (526 g, 3.9 mol) was then fed for over 2 hours at the reflux temperature. The reaction was monitored by gas chromatography. A sample the reaction mixture was quenched in isopropyl alcohol, water, and toluene. After the feed of bromomethyl-cyclopropane was completed, the reaction was aged for a total of 6 hours. The reaction mixture was then cooled to 10° C. and quenched with isopropyl alcohol (100 mL), water (1 L), and toluene (500 mL). On the work-up, the reaction mixture was acidified with HCl (300 mL) and washed with sodium carbonate solution (5%, 500 mL) in a separatory funnel followed with warm H2O until the pH was neutral. Distillation of the resulting mixture provided the product 4-cyclopropylmethoxymethyl-5-methyl-cyclohexene. heated The reaction mixture was aged for a half-hour was then fed for over 2 hours at the reflux temperature A sample the reaction mixture was quenched in isopropyl alcohol was aged for a total of 6 hours The reaction mixture was then cooled to 10° C. quenched with isopropyl alcohol (100 mL), water (1 L), and toluene (500 mL) washed with sodium carbonate solution (5%, 500 mL) in a separatory funnel Distillation of the resulting mixture

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction flask was charged with tetrahydrofuran (THF, 500 mL) and sodium amide (NaNH2, 100 g, 2.6 mol) and heated to reflux (˜65° C.). (6-Methyl-cyclohex-3-enyl)-methanol (300 g, 2.3 mol) was fed in. The reaction mixture was aged for a half-hour. Bromomethyl-cyclopropane (526 g, 3.9 mol) was then fed for over 2 hours at the reflux temperature. The reaction was monitored by gas chromatography. A sample the reaction mixture was quenched in isopropyl alcohol, water, and toluene. After the feed of bromomethyl-cyclopropane was completed, the reaction was aged for a total of 6 hours. The reaction mixture was then cooled to 10° C. and quenched with isopropyl alcohol (100 mL), water (1 L), and toluene (500 mL). On the work-up, the reaction mixture was acidified with HCl (300 mL) and washed with sodium carbonate solution (5%, 500 mL) in a separatory funnel followed with warm H2O until the pH was neutral. Distillation of the resulting mixture provided the product 4-cyclopropylmethoxymethyl-5-methyl-cyclohexene. heated The reaction mixture was aged for a half-hour was then fed for over 2 hours at the reflux temperature A sample the reaction mixture was quenched in isopropyl alcohol was aged for a total of 6 hours The reaction mixture was then cooled to 10° C. quenched with isopropyl alcohol (100 mL), water (1 L), and toluene (500 mL) washed with sodium carbonate solution (5%, 500 mL) in a separatory funnel Distillation of the resulting mixture

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

Procedure: A 500 mL round bottom flask equipped with a mechanical stirrer was charged with 18.9g (0.15 mol) 6-methyl-3-cyclohexenemethanol, and 130 mL of DMSO. Sodium hydride (4.22 g, 95% in purity; 0.167 mol) was slowly added to above mixture in ice bath over 25 min. After the above mixture was reacted at room temperature for 2 hrs. Hexyl bromide (27.3 g, 0.165 mol) was slowly added to the above mixture over 25 min. The reaction was carried at room temperature for 1 hr, then 70° C overnight. The reaction mixture was added to water (150 mL), and then extracted with chloroform (3×150 mL), washed with water (2×150 mL), dried with sodium sulfate. The solvent was evaporated and the residue distilled to give pure product. A 500 mL round bottom flask equipped with a mechanical stirrer After the above mixture was reacted at room temperature for 2 hrs 70° C overnight extracted with chloroform (3×150 mL) washed with water (2×150 mL) dried with sodium sulfate The solvent was evaporated the residue distilled to give pure product

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction flask was charged with tetrahydrofuran (THF, 500 mL) and sodium amide (NaNH2, 100 g, 2.6 mol) and heated to reflux (˜65° C.). (6-Methyl-cyclohex-3-enyl)-methanol (300 g, 2.3 mol) was fed in. The reaction mixture was aged for a half-hour. Bromomethyl-cyclopropane (526 g, 3.9 mol) was then fed for over 2 hours at the reflux temperature. The reaction was monitored by gas chromatography. A sample the reaction mixture was quenched in isopropyl alcohol, water, and toluene. After the feed of bromomethyl-cyclopropane was completed, the reaction was aged for a total of 6 hours. The reaction mixture was then cooled to 10° C. and quenched with isopropyl alcohol (100 mL), water (1 L), and toluene (500 mL). On the work-up, the reaction mixture was acidified with HCl (300 mL) and washed with sodium carbonate solution (5%, 500 mL) in a separatory funnel followed with warm H2O until the pH was neutral. Distillation of the resulting mixture provided the product 4-cyclopropylmethoxymethyl-5-methyl-cyclohexene. heated The reaction mixture was aged for a half-hour was then fed for over 2 hours at the reflux temperature A sample the reaction mixture was quenched in isopropyl alcohol was aged for a total of 6 hours The reaction mixture was then cooled to 10° C. quenched with isopropyl alcohol (100 mL), water (1 L), and toluene (500 mL) washed with sodium carbonate solution (5%, 500 mL) in a separatory funnel Distillation of the resulting mixture