Toluene → 4-Chloro-2,2-diphenyl-4-pentenenitrile

HRID 444457Notes

Reaction equation

[NH2-].[Na+].C1(C)C=CC=CC=1.[C:10]1([CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]#[N:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:25][C:26]([CH2:28]Cl)=[CH2:27]>C(OCC)C.CN(C)C=O>[Cl:25][C:26](=[CH2:27])[CH2:28][C:16]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:17]#[N:18]

Participants

Conditions

Temperature: 10 °C

Procedure

A 40.3 g. portion of sodium amide was suspended in 400 ml. of dry toluene at 70° C. and 199.6 g. of diphenylacetonitrile, dissolved in 600 ml. of hot dry toluene, was added dropwise. The mixture was stirred at 70°-100° C. for 4 hours, and an additional 500 ml. of dry toluene and 100 ml. of dimethylformamide were added. The mixture was stirred for 27 hours more. The slurry was cooled to 10° C., and 114.6 g. of 2,3-dichloropropene was added. The mixture was warmed to ambient temperature and stirred for 40 hours, and was then stirred at 90°100° C. for one hour. The mixture was then cooled to ambient temperature, diluted with a large amount of diethyl ether, washed with water and dried over magnesium sulfate. The solution was evaporated to give 265 g. of crude liquid product.

Workup

customat 70° C.
stirringThe mixture was stirred for 27 hours more
temperatureThe mixture was warmed to ambient temperature
stirringstirred for 40 hours
stirringwas then stirred at 90°100° C. for one hour
temperatureThe mixture was then cooled to ambient temperature
washwashed with water
dry with materialdried over magnesium sulfate
customThe solution was evaporated
customto give 265 g

Sources & evidence

ORD record: ord-d56a40f6368a4cda923708268d64e352
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04264521

Reaction notes

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