Hydrochloric Acid → HCID 21388393, compound

HRID 1834035Notes

Reaction equation

HRID 1834035 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=2)[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([C:21]([F:24])([F:22])[F:23])[CH:15]=2)[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21388404HCID 21388404, compound

Product 1

HCID 21388393HCID 21388393, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

59.3 g (0.163 mol) of methyl 2-(4-chloro-phenyl)-2-(4-fluoro-3-trifluoromethyl-phenoxy)-acetate are added to a solution of 15 g of sodium hydroxide in 400 ml of water. The suspension obtained is stirred and heated at the reflux temperature until a limpid solution is obtained (duration, 4 hours). The reaction mixture is cooled and acidified with a hydrochloric acid solution; an oil precipitates, which is extracted with ether. The ether phase is washed with water and dried and the solvent is driven off. The residue is triturated in petroleum ether until it crystallises, and is recrystallised from a mixture of hexane and cyclohexane (50-50). 43 g (yield: 75%) of 2-(4-chlorophenyl)-2-(4-fluoro-3-trifluoromethyl-phenoxy)-acetic acid are thus obtained. Melting point = 106° C.

Workup

  1. customThe suspension obtained
  2. temperatureheated at the reflux temperature until a limpid solution
  3. customis obtained (duration, 4 hours)
  4. temperatureThe reaction mixture is cooled
  5. customan oil precipitates
  6. extractionwhich is extracted with ether
  7. washThe ether phase is washed with water
  8. customdried
  9. customThe residue is triturated in petroleum ether until it
  10. customcrystallises
  11. customis recrystallised from a mixture of hexane and cyclohexane (50-50)

Sources & evidence

ORD record
ord-f0006b97521a4e4f8c9d37259d09dd84
Source dataset
uspto-grants-1978_01
Patent number
US04067996

Reaction notes

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