Sodium Hydroxide → HCID 54013597, compound

HRID 1277986Notes

Reaction equation

HRID 1277986 reaction equation
C([O:3][C:4]([CH:6]1[CH:8]([CH:9]=[C:10]([Br:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:7]1([CH3:20])[CH3:19])=[O:5])C.[OH-].[Na+]>C(O)C.O>[CH3:19][C:7]1([CH3:20])[CH:8]([CH:9]=[C:10]([Br:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:6]1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53782350HCID 53782350, compound

Product 1

HCID 54013597HCID 54013597, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

50 g (0.14 mol) of 2,2-dimethyl-3-(2-bromo-2-(4-chloro-phenyl)-vinyl)-cyclopropanecarboxylic acid ethyl ester were dissolved in 100 ml of ethanol, a solution of 6 g (0.15 mol) of sodium hydroxide in 100 ml of water was then added and the mixture was heated to the reflux temperature for 4 hours, while stirring. The ethanol was then distilled off under a waterpump vacuum, the residue was taken up in 300 ml of warm water and the mixture was extracted once with 300 ml of methylene chloride. The aqueous phase was separated off, acidified with concentrated hydrochloric acid and then extracted with 2 portions of 300 ml of methylene chloride. The organic phase was then separated off and dried over magnesium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation under 2 mm Hg at a bath temperature of 60° C. 37.8 g (81.9% of theory) of 2,2-dimethyl-3 -(2-bromo-2-(4-chlorophenyl)-vinyl)-cyclopropanecarboxylic acid (cis and trans, E and Z isomer mixture) were then obtained as a very viscous yellow oil. The structure was confirmed by the 1H-NMR spectrum.

Workup

  1. temperaturethe mixture was heated to the reflux temperature for 4 hours
  2. distillationThe ethanol was then distilled off under a waterpump vacuum
  3. extractionthe mixture was extracted once with 300 ml of methylene chloride
  4. customThe aqueous phase was separated off
  5. extractionextracted with 2 portions of 300 ml of methylene chloride
  6. customThe organic phase was then separated off
  7. dry with materialdried over magnesium sulphate
  8. distillationthe solvent was distilled off under a waterpump vacuum
  9. customLast residues of solvent were removed by brief incipient distillation under 2 mm Hg at a bath temperature of 60° C

Sources & evidence

ORD record
ord-acaa38f719f0462696d330c14aff2333
Source dataset
uspto-grants-1981_07
Patent number
US04279920

Reaction notes

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