Sodium Hydroxide → HCID 86740189, compound

HRID 371050Notes

Reaction equation

HRID 371050 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH:15]([C:16]([O:18]CC)=[O:17])[C:14]2([CH3:22])[CH3:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C@H:13]2[C@H:15]([C:16]([OH:18])=[O:17])[C:14]2([CH3:22])[CH3:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13150413HCID 13150413, compound

Product 1

HCID 86740189HCID 86740189, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

16 g (0.042 mol) of ethyl 3-(3-bromo-4-trifluoromethoxyphenyl)-2,2-dimethyl-cyclopropanecarboxylate were dissolved in 50 ml of ethanol, a solution of 3.4 g (0.085 mol) of sodium hydroxide in 50 ml of water was then added, and the mixture was heated under reflux for 4 hours, while stirring. The ethanol was then distilled off in the vacuum from a water jet, the residue was taken up in 300 ml of water, and the solution 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 and dried over magnesium sulphate, and the solvent was distilled off in the vacuum from a water jet. The last residues of solvent were removed by incipient distillation for a short time, at a bath temperature of 50° C./2 mm Hg. 9.8 g (66.3% of theory) of (±)cis/trans-3-(3-bromo-4-trifluoromethoxyphenyl)- 2,2-dimethyl-cyclopropanecarboxylic acid were then obtained as a yellow viscous oil. The structure was confirmed by the 1H-NMR spectrum.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. distillationThe ethanol was then distilled off in the vacuum from a water jet
  4. extractionthe solution was extracted once with 300 ml of methylene chloride
  5. customThe aqueous phase was separated off
  6. extractionextracted twice with 300 ml of methylene chloride
  7. customThe organic phase was then separated off
  8. dry with materialdried over magnesium sulphate
  9. distillationthe solvent was distilled off in the vacuum from a water jet
  10. customThe last residues of solvent were removed by incipient distillation for a short time, at a bath temperature of 50° C./2 mm Hg

Sources & evidence

ORD record
ord-eb74b9c046f84b9692851257de693261
Source dataset
uspto-grants-1985_07
Patent number
US04529557

Reaction notes

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