Water → HCID 12884350, compound

HRID 2058670Notes

Reaction equation

HRID 2058670 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:26])[C:20]([CH3:22])([CH3:21])[CH:19]1[C:23](Cl)=[O:24].[C-:27]#[N:28].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CCCCCC>[C:27]([CH:11]([O:12][C:23]([CH:19]1[C:18]([CH3:26])([CH3:17])[C:20]1([CH3:22])[CH3:21])=[O:24])[C:10]1[CH:13]=[CH:14][C:15]([F:16])=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)#[N:28]

Participants

8

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Product 1

HCID 12884350HCID 12884350, compoundYield 786%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

5 g (0.0232 mol) of 3-phenoxy-4-fluoro-benzaldehyde and 3.72 g (0.0232 mol) of 2,2,3,3-tetramethylcyclopropanecarboxylic acid chloride were together added dropwise to a mixture of 1.8 g of sodium cyanide, 2.7 ml of water, 100 ml of n-hexane and 0.6 g of tetrabutylammonium bromide at 20°-25° C., while 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 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. 67 g (78.7% of theory) of 2,2,3,3-tetramethylcyclopropanecarboxylic acid α-cyano-3-phenoxy-4-fluoro-benzyl ester were obtained as a yellow oil with a refractive index nD24 of 1.5732.

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-485062c2b53e4c358dde15565790cc9e
Source dataset
uspto-grants-1982_03
Patent number
US04318922

Reaction notes

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