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The general procedure for the synthesis of 4-hydroxycyclohexanecarbonitrile from 4-oxocyclohexanecarbonitrile was as follows: 4-oxocyclohexanecarbonitrile (10 g, 81.20 mmol, 1.00 eq.) and methanol (100 mL) were added to a 250 mL four-necked round-bottomed flask under inert nitrogen protection. Subsequently, sodium borohydride (1.52 g, 40.18 mmol, 0.50 eq.) was slowly added in an ice-water bath at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of 20 mL of aqueous ammonium chloride. The reaction mixture was extracted with ethyl acetate (2 x 100 mL), the organic layers were combined and dried with anhydrous sodium sulfate. Finally, the organic layer was concentrated under reduced pressure to afford 4-hydroxycyclohexanecarbonitrile (10.02 g, 99% yield) as a colorless oil.

[1] Patent: US2017/166584, 2017, A1. Location in patent: Paragraph 0887-0889
[2] Annales de Chimie (Cachan, France), 1955, vol. <12> 10, p. 497,531
[3] Bulletin de la Societe Chimique de France, 1954, p. 610,612
[4] Patent: WO2009/156100, 2009, A1. Location in patent: Page/Page column 156