Hydrochloric Acid → 2-Isopropyl-4-trifluoromethyl-benzoic acid

HRID 1950924Notes

Reaction equation

HRID 1950924 reaction equation
[I-].[CH:2]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[C:15]1[O:16]CC(C)(C)[N+]=1C)([CH3:4])[CH3:3].[OH-:23].[Na+].Cl>CO>[CH:2]([C:5]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:6]=1[C:15]([OH:16])=[O:23])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 666828202-(2-Isopropyl-4-trifluoromethyl-phenyl)-3,4,4-trimethyl-4,5-dihydro-oxazol-3-ium iodide

Product 1

HCID 594385402-Isopropyl-4-trifluoromethyl-benzoic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2-(2-isopropyl-4-trifluoromethyl-phenyl)-3,4,4-trimethyl-4,5-dihydro-oxazol-3-ium iodide (step 2) (1.26 g, 2.949 mmol) in 12 ml methanol were added 5N NaOH solution (11.8 ml, 58.98 mmol). The mixture was stirred in a 75° C. oil bath for 3 hours. The solution was cooled in an ice bath and acidified to pH 1 with a 5N HCl solution. The methanol was removed in vacuo. The suspension was stirred in an ice bath. The solid was filtered, washed with water and dried in vacuo to provide 618 mg (90%) of the title compound as a white solid. MS (m/e): 231.1 (M−H).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe methanol was removed in vacuo
  3. stirringThe suspension was stirred in an ice bath
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fe697d493da0493d86d2d06f6bd27418
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Reaction notes

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