Sodium Hydroxide → Permethric acid

HRID 261459Notes

Reaction equation

HRID 261459 reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([OH:9])=[O:8])[C:5]1([CH3:11])[CH3:10].[OH-].[Na+]>O>[Cl:1][C:2]([Cl:12])=[CH:3][CH:4]1[CH:6]([C:7]([OH:9])=[O:8])[C:5]1([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 41507Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid2×

Product 1

HCID 91658Permethric acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Conversion to high cis 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid (compound C acid). Sodium hydroxide (20 g, 0.5 mole) in 100 ml of water was added to the reaction mixture above with vigorous stirring and the whole was heated at 100° for 5 hours under conditions allowing for the distillation of the tert-butanol present from the Phase (a) reaction. The mixture was allowed to cool to room temperature, then washed with ether and made acidic with concentrated hydrochloric acid. The acidified mixture was extracted with ether and the ether extracts were combined, washed with brine, dried over magnesium sulfate and concentrated to give, after distillation, 18.22 g (87% yield) of 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid, bp 102°-105°/0.3 mm Hg, purity 97.3%, C/T=78/22.

Workup

  1. temperaturethe whole was heated at 100° for 5 hours under conditions
  2. distillationallowing for the distillation of the tert-butanol present from the Phase (a) reaction
  3. washwashed with ether
  4. extractionThe acidified mixture was extracted with ether
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give

Sources & evidence

ORD record
ord-7002097287ca43efa4a95f54092d8121
Source dataset
uspto-grants-1979_08
Patent number
US04166064

Reaction notes

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