S(=O)(O)[O-].[Na+].[CH3:6][C@@H:7]1[CH:12]=[CH:11][CH2:10][CH2:9][C@H:8]1[CH:13]=[O:14].[C-:15]#[N:16].[K+]>O.C(O)C>[CH3:6][C@@H:7]1[CH:12]=[CH:11][CH2:10][CH2:9][C@H:8]1[CH:13]([OH:14])[C:15]#[N:16]Sodium bisulfite (10.4 g., 0.1 mole) was dissolved in 50 ml. H2O. Absolute ethanol (50 ml.) and trans-2-methyl-3-cyclohexene-1-carbaldehyde (85%, 8.6 g., 0.07 mole) were added and the mixture heated in an oil bath at 63°-65° C. for 1.5 hours, then cooled to 15° C. in an ice-water bath. KCN (13 g., 0.2 mole) in 50 ml. H2O was added at 15°-18° C. The reaction mixture was stirred at room temperature 0.5 hour and extracted with 150 ml. ether. The ether was back-washed with 75 ml. H2O and concentrated in vacuo to yield title product as an oil, 5.5 g. Based on pnmr, the product contained 85% trans isomer (doublet at 4.6 ppm, J=4) and 15% cis isomer (doublets at 4.2 and 4.35, J=2).
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