[BH4-].[Na+].[C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH:11]=[O:12])[CH2:7][CH2:6]1)#[N:4].Cl>CO.C(OCC)C>[OH:12][CH2:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]#[N:4])[CH2:6][CH2:7]1A suspension of 829 mg of sodium borohydride in 20 ml of methanol/diethyl ether (vol. 9:1) was treated dropwise within 5 minutes at 0° C. with a solution of 3.0 g of trans-4-cyanocyclohexanecarboxaldehyde in 30 ml of methanol/diethyl ether (vol. 9:1). The reaction mixture was stirred for a further 2 hours at 10° C., then treated with 10 ml of dilute hydrochloric acid and partitioned in methylene chloride/water. The aqueous phase was extracted three times with methylene chloride. The organic phases were washed twice with water, dried over magnesium sulphate, filtered and concentrated. There were obtained 3.0 g (98%) of trans-4-(hydroxymethyl)cyclohexanecarbonitrile as a colourless oil.
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