Water → HCID 54197408, compound

HRID 1680038Notes

Reaction equation

HRID 1680038 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]([CH:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:21](Cl)=[O:22])([CH3:19])[CH3:18].[C-:31]#[N:32].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CCCCCC>[C:1]1([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]([O:13][C:21](=[O:22])[CH:20]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH:17]([CH3:19])[CH3:18])[C:31]#[N:32])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 41780012-(4-Chlorophenyl)-3-methylbutanoyl chlorideHCID 54004460HCID 54004460, compound

Product 1

HCID 54197408HCID 54197408, compoundYield 69.9%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

4.16 g (0.02 mol) of 3-(2-phenyl-vinyl)-benzaldehyde and 4.62 g (0.02 mol) of α-isoproyl-4-chlorophenyl-acetic acid chloride were added dropwise, together, to a mixture of 1.5 g of sodium cyanide, 2 ml of water, 40 ml of n-hexane and 0.5 g of tetrabutylammonium bromide at 20°-25° C., whilst stirring, and the mixture was then stirred at 20°-25° C. for 4 hours. 300 ml of toluene were then added to the reaction mixture, and the mixture was extracted by shaking twice with 300 ml of water each time. The organic phase was separated off and dried over magnesium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by subjecting the product to brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 6 g (69.9% of theory) of α-isopropyl-4-chlorophenylacetic acid 3-(2-phenylvinyl)-α-cyanobenzyl ester were obtained as a yellow oil with the refractive index nD22 : 1.5879 (isomer mixture with a cis-stilbene proportion of about 90%).

Workup

  1. stirringthe mixture was then stirred at 20°-25° C. for 4 hours
  2. extractionthe mixture was extracted
  3. stirringby shaking twice with 300 ml of water each time
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulphate
  6. distillationthe solvent was distilled off under a waterpump vacuum
  7. customLast residues of solvent were removed
  8. distillationto brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-0b2028fe58ad41a28c90549835237854
Source dataset
uspto-grants-1981_06
Patent number
US04271186

Reaction notes

Loading…