Tetrahydrofuran → Cypermethrin

HRID 1155002Notes

Reaction equation

HRID 1155002 reaction equation
[C-:1]#[N:2].[Na+].O1CCCC1.[O:9]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:24][C:25]([Cl:35])=[CH:26][CH:27]1[CH:29]([C:30](Cl)=[O:31])[C:28]1([CH3:34])[CH3:33]>O1CCCC1.O.O>[Cl:24][C:25]([Cl:35])=[CH:26][CH:27]1[CH:29]([C:30]([O:20][CH:19]([C:1]#[N:2])[C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([O:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:17]=2)=[O:31])[C:28]1([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8929Sodium CyanideHCID 382843-PhenoxybenzaldehydeHCID 94551Permethric chloride

Product 1

HCID 2912Cypermethrin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Sodium cyanide (0.765 g, 15.6 mmole), along with 20 ml of 2:1 tetrahydrofuran:water by volume, was charged to a reaction flask, and the resultant solution was stirred while the temperature was raised to 40°. 3-Phenoxybenzaldehyde (2.06 g, 10 mmole) was added in 5 ml of the tetrahydrofuran/water mixture (25 ml total). 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (2.84 g, 12.5 mmole) was then added to the flask dropwise over a 10 minute period. The temperature of the reaction mixture was maintained between 40° and 40° during the acyl chloride addition. The reaction mixture was then stirred at 40° for an additional 2 hours, after which it was extracted three times with 15 ml portions of n-heptane. The combined organic phases were washed once with water (15 ml), once with a 2 N aqueous sodium hydroxide solution (15 ml), three more times with water (15 ml) portions), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. A quantitative yield of α-cyano-3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate remained as the residue.

Workup

  1. temperaturewas raised to 40°
  2. extractionafter which it was extracted three times with 15 ml portions of n-heptane
  3. washThe combined organic phases were washed once with water (15 ml), once with a 2 N aqueous sodium hydroxide solution (15 ml), three more times with water (15 ml) portions),
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1cd8d8877f94e3f9f2e1cf9b4a156ce
Source dataset
uspto-grants-1981_11
Patent number
US04299776

Reaction notes

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