[NH2-].[Na+].[CH3:3][CH:4]1[CH:9]([CH2:10][OH:11])[CH2:8][CH:7]=[CH:6][CH2:5]1.Br[CH2:13][CH:14]1[CH2:16][CH2:15]1>O1CCCC1>[CH:14]1([CH2:13][O:11][CH2:10][CH:9]2[CH:4]([CH3:3])[CH2:5][CH:6]=[CH:7][CH2:8]2)[CH2:16][CH2:15]1A 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.
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