Toluene → 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonitrile

HRID 2057515

Reaction equation

Cl[CH:2]([CH2:12][C:13]([Cl:16])([Cl:15])Cl)[C:3]([CH3:11])([CH3:10])[CH:4]([C:8]#[N:9])C(O)=O.C1(C)C=CC=CC=1>CN(C)C=O>[Cl:16][C:13]([Cl:15])=[CH:12][CH:2]1[C:3]([CH3:10])([CH3:11])[CH:4]1[C:8]#[N:9]

Participants

Conditions

Temperature: 145 °C

Procedure

A solution of 4-chloro-2-cyano-3,3-dimethyl-6,6,6-trichlorohexanoic acid (6.14 g) in dimethyl formamide (12 ml) was stirred at 145° C. for 4 hours under an ammonia atmosphere at initially 5 bar pressure. After release of the pressure the mixture was stirred for another 6 hours at 145° C. After cooling, over 90% of the solvent was flashed off (bath temperature max. 60° C., pressure 12 mmHg). The residue was mixed with toluene and subsequently washed with aqueous hydrochloric acid and aqueous sodium bicarbonate. After drying of the organic phase the solvent was removed under reduced pressure to yield 3.3 g of the required 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane nitrile (97% pure, 89% yield).

Workup

custom(bath temperature max. 60° C., pressure 12 mmHg)
washsubsequently washed with aqueous hydrochloric acid and aqueous sodium bicarbonate
customAfter drying of the organic phase the solvent
customwas removed under reduced pressure

Sources & evidence

ORD record: ord-53db2e25760d41c08e88f52e34312f8c
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04211720

Linked notes

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