1-Chloro-4-nitrobenzene → 2-(4-Nitrophenyl)-2-phenylpropanenitrile

HRID 1494687Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:13][CH:14]([C:21]#[N:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH3:13])[C:21]#[N:22])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 10 °C

Procedure

This compound is synthesized according to Makosza, et al with some modifications (Makosza, M., et al, Tetrahedron (1974), 30: 3723). A solution of 4-chloronitrobenzene (31.5 g, 0.2 mol) in pyridine (100 mL) is added dropwise to a vigorously stirred suspension of KOH (fine powder 70.0 g) and α-methylbenzylcyanide (26.2 g, 0.2 mol) in pyridine (150 mL), with the reaction temperature being maintained at 10° C. The reaction mixture is stirred for 24 hours at 25° C., and poured onto an excess of HCl-ice mixture. The acidic aqueous mixture is extracted with benzene, the organic phase washed with brine, dried (Na2SO4), and the benzene evaporated under vacuum. A crude product 42.5 g (84 wt %) results and is recrystallized from isopropanol-petroleum ether to give Compound 7 as white crystals,

Workup

customThis compound is synthesized
extractionThe acidic aqueous mixture is extracted with benzene
washthe organic phase washed with brine
dry with materialdried (Na2SO4)
customthe benzene evaporated under vacuum
customA crude product 42.5 g (84 wt %) results
customis recrystallized from isopropanol-petroleum ether

Sources & evidence

ORD record: ord-c00df3bc34d647ec85bb2691ef4a8490
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05026897

Reaction notes

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