Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | 4-Fluoro-3-phenoxybenzaldehyde | HCID 110068 | — |
| Reactant | HCID 53824254 | HCID 53824254 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 54440363 | HCID 54440363 | 62.6% |
Reaction Steps
4.32 g (0.02 mol) of 3-phenoxy-4-fluoro-benzaldehyde and 7.1 g (0.02 mol) of 2,2-dimethyl-3-(2-chloro-2-(4-trifluoromethoxy-phenyl)-vinyl)-cyclopropanecarboxylic acid chloride were together added dropwise to a mixture of 1.6 g of sodium cyanide, 2.5 ml of water, 100 ml of n-hexane and 0.5 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 subsequently added, and the reaction 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 brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 7 g (62.6% of theory) of 2,2-dimethyl-3-(2-chloro-2-(4-trifluoromethoxy-phenyl)-vinyl)-cyclopropanecarboxylic acid 3-phenoxy-4 -fluoro-α-cyano-benzyl ester were obtained as a viscous oil. The structure was confirmed by the 1H-NMR spectrum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04316913 |
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| Source dataset | uspto-grants-1982_02 |
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| ORD ID | ord-9d9027b1e39f42d59851176312498eba |
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| Source note | uspto-grants-1982_02 |
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