Diethyl Ether → Permethric acid

HRID 127712

Reaction equation

HRID 127712 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 solution of 2.1 grams (0.086 mole) of cyano(6-(3-fluorophenoxy)-2-pyridine)methanol and 2.0 grams (0.0088 mole) of 2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane carboxylic acid chloride in 50 milliliters of anhydrous ether was added 3 milliliters of triethylamine. A white precipitate separated out immediately. The reaction mixture was stirred at room temperature for one-half (1/2) hours. The mixture was successively washed with water, dilute hydrochloric acid, dilute sodium hydroxide, dilute sodium bisulfite, dilute hydrochloric acid and water and thereafter dried over anhydrous magnesium sulfate and concentrated under vacuo to give 3.5 grams of crude 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(3-fluorophenoxy)-2-pyridinyl)methyl ester product as a residue. This residue was purified by distillation under reduced pressure to give 3.2 grams of a viscous yellow oil having a refractive index of nD25 =1.5538. The structure of the product was confirmed by its nuclear magnetic resonance spectrum (NMR). In addition, upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 57.91, 3.95 and 6.16 percent, respectively, as compared with the theoretical contents of 57.94, 3.94 and 6.44 percent, respectively, as calculated for the above-named compound (Compound No. 3).

Workup

  1. customA white precipitate separated out immediately
  2. washThe mixture was successively washed with water, dilute hydrochloric acid, dilute sodium hydroxide, dilute sodium bisulfite, dilute hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-e0dbd40929fa4fe3a6f7b0b0f4776131
Source dataset
uspto-grants-1981_03
Patent number
US04256893

Linked notes

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