Toluene → HCID 13953402, compound

HRID 2107134Notes

Reaction equation

HRID 2107134 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:23]=[CH:22][C:14]([CH2:15][CH2:16]CS([O-])(=O)=O)=[CH:13][CH:12]=1.C1(C)C=CC=CC=1.[OH-].[Na+]>O.CS(C)=O>[Cl:10][C:11]1[CH:23]=[CH:22][C:14]([CH2:15][CH2:16][CH:1]([C:8]#[N:9])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8794PhenylacetonitrileHCID 14798Sodium Hydroxide2×HCID 23047341HCID 23047341, compound

Product 1

HCID 13953402HCID 13953402, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

This product was also obtained by charging a reaction vessel with 58.6 gm of benzylcyanide (0.5 mole), 116.8 gm of 4-chlorophenethylmethanesulfonate (0.5 mole), 500 ml of toluene and 500 ml of dimethylsulfoxide. The mixture was cooled to about 5° C. and 50% sodium hydroxide was added slowly with rapid mixing while maintaining the temperature at about 5°-10° C. After the addition of the sodium hydroxide (about 1.5 hours), the mixture was allowed to warm to room temperature and then stirred for another three hours. One liter of water was added to the mixture and it was transferred to a separatory funnel where it was extracted with ether; the combined ether extracts were sequentially washed with 5% hydrochloric acid, water and brine. The liquid obtained after solvent removal was distilled to obtain 102 gm of 3-(4-chlorophenyl)-1-cyano1-phenylpropane.

Workup

  1. customThis product was also obtained
  2. additionwith rapid mixing
  3. temperaturewhile maintaining the temperature at about 5°-10° C
  4. temperatureto warm to room temperature
  5. customwas transferred to a separatory funnel
  6. extractionwhere it was extracted with ether
  7. washthe combined ether extracts were sequentially washed with 5% hydrochloric acid, water and brine
  8. customThe liquid obtained
  9. customafter solvent removal
  10. distillationwas distilled

Sources & evidence

ORD record
ord-b0ea40ca99ca44a3bc670e5b743a230f
Source dataset
uspto-grants-1990_06
Patent number
US04933339

Reaction notes

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