Acetic Acid → 2-Methyl-2-[3-(trifluoromethyl)phenyl]propanoic acid

HRID 651425Notes

Reaction equation

HRID 651425 reaction equation
C[O:2][C:3](=[O:17])[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)([CH3:6])[CH3:5].C(O)(=O)C.S(=O)(=O)(O)O>O>[CH3:6][C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=1)([CH3:5])[C:3]([OH:17])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 604466Methyl 2-methyl-2-[3-(trifluoromethyl)phenyl]propanoate

Product 1

HCID 177883242-Methyl-2-[3-(trifluoromethyl)phenyl]propanoic acidYield 71.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

α,α-Dimethyl-(3-trifluoromethylphenyl)acetic acid methyl ester (24.6 g, 0.1 mol), acetic acid (150 ml), water (75ml) and sulfuric acid (36 g, 0.36 mol) are combined. The reaction is refluxed for 3 hours and stirred at room temperature for 3 days. The reaction is concentrated to half its original volume and added to ethyl acetate and washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 16.6 g α,α-dimethyl-(3-trifluoromethylphenyl)acetic acid as a white solid. 1H NMR CDCl3 1.63 (6H,s) 7.45-7.65 (4H, m)

Workup

  1. temperatureThe reaction is refluxed for 3 hours
  2. concentrationThe reaction is concentrated to half its original volume
  3. additionadded to ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da429a9e92ff4a08b7d0cfe55be30454
Source dataset
uspto-grants-2001_08
Patent number
US06281219B1

Reaction notes

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