Dimethyl Sulfoxide → 4-[p-(2-Cyanoethyl)phenyl]pentylcyclohexane

HRID 2309287Notes

Reaction equation

HRID 2309287 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:20])[CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:6][CH:5]=1.CS(C)=O.[C-:25]#[N:26].[Na+].Cl[O-].[Na+]>O>[C:25]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:20])[CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:6][CH:5]=1)#[N:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 201862644-[p-(2-Chloroethyl)phenyl]pentylcyclohexaneHCID 23665760Sodium Hypochlorite

Product 1

HCID 201862634-[p-(2-Cyanoethyl)phenyl]pentylcyclohexane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9 Grams of the 4-[p-(2-chloroethyl)phenyl]pentylcyclohexane, 100 ml of dimethyl sulfoxide ((CH3)2SO) and 23 g of sodium cyanide (NaCN) were stirred together at 140° to 150° C. for 2 hours. After the resulting mixture was cooled, a 10% aqueous sodium hypochlorite (NaClO) solution was added. Further, water was added thereto, and the precipitate was recrystallized from ligroin to obtain 4-[p-(2-cyanoethyl)phenyl]pentylcyclohexane. The melting point of this compound was 44° to 46° C.

Workup

  1. temperatureAfter the resulting mixture was cooled
  2. customthe precipitate was recrystallized from ligroin

Sources & evidence

ORD record
ord-61da5bc4ea0f469096927aedc166b160
Source dataset
uspto-grants-1987_09
Patent number
US04694098

Reaction notes

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