Sodium Hydroxide → HCID 54323314, compound

HRID 848761Notes

Reaction equation

HRID 848761 reaction equation
C([O:3][C:4]([CH:6]1[CH:8]([CH:9]=[C:10]([O:15][CH3:16])[C:11]([F:14])([F:13])[F:12])[C:7]1([CH3:18])[CH3:17])=[O:5])C.[OH-].[Na+]>C(O)C.O>[CH3:17][C:7]1([CH3:18])[CH:8]([CH:9]=[C:10]([O:15][CH3:16])[C:11]([F:14])([F:13])[F:12])[CH:6]1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54558857HCID 54558857, compound

Product 1

HCID 54323314HCID 54323314, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

16.6 g (0.0624 mol) of 2,2-dimethyl-3-(3,3,3-trifluoro-2-methoxy-prop-1-enyl)-cyclopropanecarboxylic acid ethyl ester were dissolved in 100 ml of ethanol, a solution of 2.9 g (0.073 mol) of sodium hydroxide in 75 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 water and the aqueous mixture was extracted once with 300 ml of methylene chloride. The aqueous phase was separated off, acidified with concentrated hydrochloric acid and then extracted twice with 300 ml of methylene chloride. The organic phase was then separated off over magnesium sulphate, dried and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 50° C. under 2 mbar. 9 g (60.6% of theory) of 2,2-dimethyl-3-(3,3,3-trifluoro-2-methoxy-prop-1-enyl)-cyclopropanecarboxylic acid were then obtained as a yellow viscous oil.

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 aqueous mixture was extracted once with 300 ml of methylene chloride
  4. customThe aqueous phase was separated off
  5. extractionextracted twice with 300 ml of methylene chloride
  6. customThe organic phase was then separated off over magnesium sulphate
  7. customdried
  8. distillationthe solvent was distilled off under a waterpump vacuum
  9. customLast residues of solvent were removed by brief incipient distillation at a bath temperature of 50° C. under 2 mbar

Sources & evidence

ORD record
ord-4a99efef8ef34620b96cb0380f7dfab8
Source dataset
uspto-grants-1981_10
Patent number
US04297366

Reaction notes

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