Hydrochloric Acid → HCID 178447948, compound

HRID 1250129Notes

Reaction equation

HRID 1250129 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]=[CH:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].Cl.C(O)C>O>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7](/[CH:10]=[CH:11]/[C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 178447949HCID 178447949, compound

Product 1

HCID 178447948HCID 178447948, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This nitrile in an amount of 11.7 g (0.05 ml) was added to a mixture of 13.9 g (0.07 ml) of dihydrated sodium benzenesufinate, 12 ml of 6N-HCl, and 70 ml of ethanol, and reacted under reflux for 4 hours. After finishing of the reaction, 50 ml of water was added to the reaction product and then extracted with 150 ml of toluene. The organic layer thus obtained was washed with saturated aqueous sodium carbonate solution thrice and with water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: toluene) to obtain 12.0 g of a crude (E)-4-(2-(trans-4-propylcyclohexyl)vinyl)benzonitrile.

Workup

  1. customreacted
  2. temperatureunder reflux for 4 hours
  3. additionwas added to the reaction product
  4. extractionextracted with 150 ml of toluene
  5. customThe organic layer thus obtained
  6. washwas washed with saturated aqueous sodium carbonate solution thrice and with water thrice
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-8401e86d5df94a54a6afd24d120253dd
Source dataset
uspto-grants-2002_01
Patent number
US06337034B1

Reaction notes

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