Diethyl Ether → Permethric acid

HRID 127711Notes

Reaction equation

HRID 127711 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[CH:3]1[C:9](Cl)=[O:10].C(N(CC)CC)C.CC[O:22]CC>>[Cl:7][C:6]([Cl:8])=[CH:5][CH:4]1[CH:3]([C:9]([OH:22])=[O:10])[C:2]1([CH3:12])[CH3:1]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 94551Permethric chloride

Product 1

HCID 91658Permethric acid

Procedure

To a cooled solution (10°-15° C.) of 2.0 grams (0.009 mole) of cyano(6-phenoxy-2-pyridine)methanol and 2.0 grams (0.009 mole) of 2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane carboxylic acid chloride in 25 milliliters of anhydrous ether was added 1 milliliter of triethylamine. A white precipitate separated out immediately. The reaction mixture was stirred at room temperature for one-half (1/2) hour. The mixture was diluted with 50 milliliters of water and extracted thoroughly with ether. The ether extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under vacuo to give 3.4 grams of crude 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester product as a thick brown oil. This oil was purified by distillation under reduced pressure to give 1.8 grams of a light brown oil boiling at 190°-200° C. at 0.1-0.2 milliliters of mercury (mm). The oil had a refractive index of nD25 =1.5264. The structure of the product was confirmed by its nuclear magnetic resonance spectrum (NMR). Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 60.28, 4.47 and 6.62 percent, respectively, as compared with the theoretical contents of 60.44, 4.35 and 6.71 percent respectively, as calculated for the above compound. (Compound No. 1).

Workup

  1. customA white precipitate separated out immediately
  2. additionThe mixture was diluted with 50 milliliters of water
  3. extractionextracted thoroughly with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-46cec42a8e034447ba2bc987107317de
Source dataset
uspto-grants-1981_03
Patent number
US04256893

Reaction notes

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