Hydrochloric Acid → 4-CHLORO-gamma-(1-OXOETHYL)-beta-METHYLBENZENEBUTANENITRILE

HRID 1995633Notes

Reaction equation

HRID 1995633 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[C:12](#[N:16])/[CH:13]=[CH:14]/[CH3:15].Cl>C(O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9](=[O:11])[CH3:10])[CH:14]([CH3:15])[CH2:13][C:12]#[N:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 796991-(p-Chlorophenyl)acetoneHCID 637921Crotononitrile

Product 1

HCID 135028694-CHLORO-gamma-(1-OXOETHYL)-beta-METHYLBENZENEBUTANENITRILE

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

Triton B (5.85 ml) was added dropwise to 4-chlorophenylacetone (21.8 grams) in 78 ml of tert. butanol. Next crotononitrile (9.17 grams) was likewise added with initial cooling to lower the temperature to about 20° C. Since the reaction was not exothermic, no additional cooling was necessary after the desired temperature was reached. The reaction was then heated to 65° C. for 21/2 hours and, after chilling in an ice bath, 262 ml of 1 N HCl was added in portions. Next the reaction mixture was extracted with ether, washed with water, dried, and evaporated in vacuo. An oil resulted which was distilled under vacuum, yield 18.6 grams, b.p. 130°-131° C.

Workup

  1. temperaturewith initial cooling
  2. customto about 20° C
  3. temperatureno additional cooling
  4. temperatureafter chilling in an ice bath
  5. extractionNext the reaction mixture was extracted with ether
  6. washwashed with water
  7. customdried
  8. customevaporated in vacuo
  9. customAn oil resulted which
  10. distillationwas distilled under vacuum, yield 18.6 grams, b.p. 130°-131° C.

Sources & evidence

ORD record
ord-0dd21bb665bc45c1968f04407990635b
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

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