536-59-4

2111-75-3

536-59-4

GENERAL STEPS: Example 13: The hydrogenation reaction for the synthesis of (4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol from 4-(prop-1-en-2-yl)cyclohex-1-enecyclohexene carboxaldehyde was carried out in a stainless steel autoclave equipped with a glass inner tube. The autoclave was pre-charged with [Cu(NO3)(PPh3)2] (11.7 mg, 0.018 mmol) and DPPB (7.7 mg, 0.018 mmol). Subsequently, the atmosphere inside the autoclave was replaced with nitrogen. An ethanol solution of sodium hydroxide (0.03 M, 6.0 mL, 0.18 mmol) and 4-(prop-1-en-2-yl)cyclohex-1-enecarboxaldehyde (2.02 mL, 9 mmol) was added to the autoclave. The reaction was stirred at hydrogen pressure of 5 MPa and 50 °C for 16 hours. Upon completion of the reaction, hydrogen was carefully released and the reaction conversion (>99%) was analyzed by gas chromatography (GC). The reaction mixture was concentrated and purified by silica gel column chromatography to give 1.26 g of the target product (4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol.