Water → HCID 67991653, compound

HRID 1979818Notes

Reaction equation

HRID 1979818 reaction equation
ClC([C@H:13]1[C@H:15]([C:16](Cl)=[O:17])[C:14]1([CH3:20])[CH3:19])C(Cl)(Cl)C1C=CC(Cl)=CC=1.[O:21]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[F:36])[CH:31]=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C-:37]#[N:38].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CCCCCC>[C:37]([CH:31]([O:32][C:16]([CH:15]1[CH2:13][C:14]1([CH3:20])[CH3:19])=[O:17])[C:30]1[CH:33]=[CH:34][C:35]([F:36])=[C:28]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:29]=1)#[N:38]

Participants

8

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 131713965HCID 131713965, compound

Product 1

HCID 67991653HCID 67991653, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

6.36 g (0.017 mole) of trans-3-(1,2,2-trichloro-2-(4-chloro-phenyl)-ethyl)-2,2-dimethyl-cyclo-propane-1-carboxylic acid chloride and 3,67 g (0.017 mole) of 3-phenoxy-4-fluoro-benzaldehyde were together added dropwise to a mixture of 1.13 g of sodium cyanide, 1.7 ml of water, 100 ml of n-hexane and 0.6 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 subsequently added to the reaction mixture, and the mixture was extracted twice by shaking 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 brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 8.5 g (86% of theory) of trans-3-(1,2,2-trichloro-2-(4-chloro-phenyl)-ethyl)-ethyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid α-cyano-3-phenoxy-4-fluorobenzyl ester were obtained as a viscous oil. ##STR35##

Workup

  1. stirringthe mixture was then stirred at 20°-25° C. for 4 hours
  2. extractionthe mixture was extracted twice
  3. stirringby shaking 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 by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-c4fe2437e2f14ab69437906e03ef6bce
Source dataset
uspto-grants-1984_11
Patent number
US04482731

Reaction notes

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