Acrylonitrile → HCID 19962413, compound

HRID 2051367Notes

Reaction equation

HRID 2051367 reaction equation
Cl[C:2]([Cl:13])([Cl:12])[C:3]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[C:14](#[N:17])[CH:15]=[CH2:16].[ClH:18].N1C=CC=CC=1>[Cu].S1(CCCC1)(=O)=O>[C:14]([CH:15]([Cl:18])[CH2:16][C:2]([Cl:12])([Cl:13])[C:3]([O:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:4])#[N:17]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 284970Phenyl trichloroacetateHCID 10176127Pyridinium chloride

Product 1

HCID 19962413HCID 19962413, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 31347SulfolaneSolvent

Conditions

Temperature
125 °C

Procedure

51 g of phenyl trichloroacetate, 17.5 ml of acrylonitrile, 0.88 g of cuprous chloride, 0.3 g of pyridine hydrochloride and 80 ml of anhydrous sulfolane were charged into a glass lined pressure reactor and heated with stirring at 125° C. for 10 hours. After cooling to ambient temperature, the brown reaction mixture was found to be homogeneous but for undissolved copper salts. GLC analysis indicated a yield of 76% (±1.5%) of the title compound based on phenyl trichloroacetate. The title compound was isolated by pouring the reaction mixture into water, extracting with several portions of methyl t-butyl ether and washing the organic phase with water. Drying (MgSO4) and subsequent removal of the combined organic extract by evaporation under reduced pressure yielded a light brown viscous oil which crystallized slowly on standing at ambient temperature. The resulting crystals were recrystallized from ether-petroleum ether (60-80) to give colorless needles of phenyl 4-cyano-2,2,4-trichlorobutyrate, m.p. 51.5°-52.5° C.;

Workup

  1. temperatureheated
  2. temperatureAfter cooling to ambient temperature

Sources & evidence

ORD record
ord-3ef176c20e93462fb5b95a7b9e0bcf36
Source dataset
uspto-grants-1991_05
Patent number
US05017705

Reaction notes

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