Hydrochloric Acid → 2-Chloro-4-trifluoromethylphenylacetic acid

HRID 1167812Notes

Reaction equation

HRID 1167812 reaction equation
C([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[Cl:18])(C)(C)C.Cl>O1CCOCC1.CCOCC>[Cl:18][C:9]1[CH:10]=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:12]=[CH:13][C:8]=1[CH2:7][C:6]([OH:19])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12088184(2-Chloro-4-trifluoromethylphenyl)-acetic acid tert-butyl ester

Product 1

HCID 120881852-Chloro-4-trifluoromethylphenylacetic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (2-chloro-4-trifluoromethylphenyl)-acetic acid tert-butyl ester (40 g, 135.7 mmol) in dioxane (100 mL) containing conc. HCl (31.3 mL) was stirred at 50° C. for 5 h. After cooling the mixture to r.t., it was diluted with Et2O and the organic layer was washed with H2O (3×). The organic phase was dried (MgSO4) and the solvent was removed in vacuo. Recrystallization of the residue with AcOEt-hexane yielded the title compound as a solid showing: 1H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H), 7.55 (dd, 1H, J=1.0, 8.0 Hz), 7.47 (d, 1H, J=8.0 Hz), 3.92 (s, 2H). MS (ESI) m/z 237 (M−H)−.

Workup

  1. temperatureAfter cooling the mixture to r.t.
  2. washthe organic layer was washed with H2O (3×)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customRecrystallization of the residue with AcOEt-hexane

Sources & evidence

ORD record
ord-d79b348a875241a9b85db827493d691c
Source dataset
uspto-grants-2003_09
Patent number
US06620838B1

Reaction notes

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