Sodium Hydroxide → Permethric acid

HRID 979324Notes

Reaction equation

HRID 979324 reaction equation
C[O:2][C:3]([C:5]1(C(OC)=O)[CH:7]([CH2:8][C:9](Cl)([Cl:11])[Cl:10])[C:6]1([CH3:14])[CH3:13])=[O:4].[OH-].[Na+]>CO>[Cl:10][C:9]([Cl:11])=[CH:8][CH:7]1[CH:5]([C:3]([OH:4])=[O:2])[C:6]1([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13048700HCID 13048700, compound

Product 1

HCID 91658Permethric acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,1-dimethoxycarbonyl-2,2-di-methyl-3-(2,2,2-trichloroethyl)cyclopropane (8.7 g, 27.3 mmoles) prepared according to the procedure of Example 5, methanol (8 ml) and 20 percent aqueous NaOH (35 ml, 175 mmoles) is heated at 100° C. for 5 hours. Acidification of the solution with concentrated HCl precipitates 2(2,2-dichlorovinyl)-3,3-dimethylcyclopropane dicarboxylic acid (6.44 g, 93 percent) which is subjected to bulb-to-bulb distillation at 0.3 mm Hg, 110° C.-150° C. The monoacid, 2(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylic acid (5.31 g), distills as it is formed from decarboxylation in about 100 percent yield. The structure of the monoacid is confirmed by its infrared and nuclear magnetic resonance spectra.

Workup

  1. customprepared
  2. customAcidification of the solution with concentrated HCl precipitates 2(2,2-dichlorovinyl)-3,3-dimethylcyclopropane dicarboxylic acid (6.44 g, 93 percent) which
  3. distillationis subjected to bulb-to-bulb distillation at 0.3 mm Hg, 110° C.-150° C
  4. distillationThe monoacid, 2(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylic acid (5.31 g), distills as it
  5. customis formed from decarboxylation in about 100 percent yield

Sources & evidence

ORD record
ord-d4dfa8dfbb8f4f639571cf4bd3f33f36
Source dataset
uspto-grants-1987_05
Patent number
US04667050

Reaction notes

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