Methanol → 2-Methoxy-3-methyl-4-trifluoromethyl-benzoic acid

HRID 659202Notes

Reaction equation

HRID 659202 reaction equation
[I-].[CH3:2][O:3][C:4]1[C:9]([CH3:10])=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[C:15]1[O:16]CC(C)(C)[N+]=1C.C[OH:24]>[OH-].[Na+]>[CH3:2][O:3][C:4]1[C:9]([CH3:10])=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:7]=[CH:6][C:5]=1[C:15]([OH:16])=[O:24]

Participants

4

Reactant 2

HCID 887MethanolHCID 666807482-(2-Methoxy-3-methyl-4-trifluoromethyl-phenyl)-3,4,4-trimethyl-4,5-dihydro-oxazol-3-ium iodide

Product 1

HCID 580629012-Methoxy-3-methyl-4-trifluoromethyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 515 mg (1.2 mmol) 2-(2-methoxy-3-methyl-4-trifluoromethyl-phenyl)-3,4,4-trimethyl-4,5-dihydro-oxazol-3-ium iodide in 5 ml methanol and 5 ml 20% NaOH was heated to 70° C. for 17 h. The yellow solution was cooled to rt, methanol was distilled off, the residue acidified with conc. HCl to pH 1 and extracted three times with tert-butyl methyl ether. The combined organic phases were washed twice with brine, dried over Na2SO4, filtered and evaporated: 2-Methoxy-3-methyl-4-trifluoromethyl-benzoic acid was obtained as yellow solid: MS (ISN): 233.04 ((M−H)−).

Workup

  1. distillationmethanol was distilled off
  2. extractionextracted three times with tert-butyl methyl ether
  3. washThe combined organic phases were washed twice with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7f014fe8109544448c077e901cc590d6
Source dataset
uspto-grants-2011_12
Patent number
US08080541B2

Reaction notes

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