Water → Fenvalerate

HRID 2420273Notes

Reaction equation

HRID 2420273 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:27]([CH3:29])[CH3:28])[C:24](Cl)=[O:25])=[CH:19][CH:18]=1.[C-:30]#[N:31].[Na+].O>C1C=CC=CC=1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:27]([CH3:29])[CH3:28])[C:24]([O:12][CH:11]([C:30]#[N:31])[C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)=[O:25])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8929Sodium Cyanide3×HCID 382843-PhenoxybenzaldehydeHCID 41780012-(4-Chlorophenyl)-3-methylbutanoyl chloride2×

Product 1

HCID 3347Fenvalerate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 50 ml round-bottomed flask equipped with a magnetic stirrer was charged with 10 mmol of 3-phenoxybenzaldehyde, 10.0 or 10.5 mmol of 2-(4-chlorophenyl)-3-methylbutanoyl chloride, 12 mmol of sodium cyanide, 0.02 ml of water and 20 ml of an aprotic solvent. The molar ratio of water to sodium cyanide was 0.105, solid NaCN being present. Thirteen experiments were conducted in this manner, see Table IV, stating which solvents were used. Experiments 1, 2, 3, 4, 8 and 9 were conducted with 10.0 and the other experiments with 10.5 mmol of 2-(4-chlorophenyl)-3-methylbutanoyl chloride. The petroleum ether used in experiment 3 consisted of 97% by weight of alkanes and 3% by weight of benzene and had a boiling range at atmospheric pressure between 62° and 82° C. The ester remained in solution during the reaction in experiments 3 and 4. The reaction mixture obtained in experiment 4 was filtered and the cyclohexane was flashed from the filtrate to give the ester wanted as a colorless oil in quantitative yield. Table IV also presents the yields of the desired ester. Comparison of the yields shows that alkanes and cycloalkanes are the best solvents.

Workup

  1. customA 50 ml round-bottomed flask equipped with a magnetic stirrer
  2. customat atmospheric pressure between 62° and 82° C
  3. customThe reaction mixture obtained in experiment 4
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-7481c3aa419245d1acbe69c608ee9d98
Source dataset
uspto-grants-1978_08
Patent number
US04110360

Reaction notes

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