Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate → 4-Oxo-1-phenylcyclohexanenitrile

HRID 1095492Notes

Reaction equation

COC([CH:5]1[CH2:10][C:9]([C:17]#[N:18])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:19])=O>OS(O)(=O)=O.C(O)(=O)C.O>[C:17]([C:9]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][C:6](=[O:19])[CH2:5][CH2:10]1)#[N:18]

Participants

Conditions

Temperature: 100 °C

Procedure

5-Cyano-2-oxo-5-phenylcyclohexanecarboxylic acid methyl ester (7.71 g, 0.03 mol) was dissolved in 10 per cent strength H2SO4 and concentrated acetic acid (240 ml). The reaction mixture was stirred at 100° C. for 24 h. The course of the reaction was monitored by TLC. For working up, the mixture was diluted with water (400 ml), while cooling with ice, and extracted with ethyl acetate (3×100 ml). The organic phase was then washed thoroughly with water (6×100 ml), saturated sodium bicarbonate solution (10×100 ml) and saturated sodium chloride solution (1×100 ml). After drying with Na2SO4, the solvent was distilled off on a rotary evaporator. It was possible to isolate the desired product in a yield of 5.46 g (92%) with a melting point of 106-107° C.

Workup

temperaturewhile cooling with ice
extractionextracted with ethyl acetate (3×100 ml)
washThe organic phase was then washed thoroughly with water (6×100 ml), saturated sodium bicarbonate solution (10×100 ml) and saturated sodium chloride solution (1×100 ml)
dry with materialAfter drying with Na2SO4
distillationthe solvent was distilled off on a rotary evaporator

Sources & evidence

ORD record: ord-ac3343024c13479c946f437bc4d788f8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138187B2

Reaction notes

Loading…