Lithium hydroxide, monohydrate → 2-(2,6-Dimethylphenyl)acetic acid

HRID 2063518Notes

Reaction equation

HRID 2063518 reaction equation
C([O:3][C:4](=[O:14])[CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])C.O.[OH-].[Li+]>C1COCC1.O>[CH3:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:13])[C:6]=1[CH2:5][C:4]([OH:14])=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54752301Ethyl 2-(2,6-dimethylphenyl)acetate

Product 1

HCID 198401152-(2,6-Dimethylphenyl)acetic acidYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (2,6-dimethyl-phenyl)-acetic acid ethyl ester (13.3 g, 69.2 mmol) in THF (550 mL) and water (224 mL) was added lithium hydroxide monohydrate (23.2 g, 553 mmol). The resulting mixture was stirred vigorously at rt. After 72 h, the mixture was heated to 50° C. for an additional 24 h. The mixture was cooled to rt and concentrated. To the resulting residue was added aqueous 2 N HCl (300 mL) to afford a colorless precipitate. The precipitate was collected by vacuum filtration and further purified by FCC to provide a colorless solid (8.9 g, 78%). MS (ESI): mass calcd. for C10H12O2, 164.1; m/z found, 163.1 [M−H]+. 1H NMR (CDCl3): 7.17-6.90 (m, 3H), 3.72 (s, 2H), 2.33 (s, 6H).

Workup

  1. temperaturethe mixture was heated to 50° C. for an additional 24 h
  2. temperatureThe mixture was cooled to rt
  3. concentrationconcentrated
  4. additionTo the resulting residue was added aqueous 2 N HCl (300 mL)
  5. customto afford a colorless precipitate
  6. filtrationThe precipitate was collected by vacuum filtration
  7. customfurther purified by FCC

Sources & evidence

ORD record
ord-cce085a9c6e24d5e86c3279cfcc0b056
Source dataset
uspto-grants-2012_10
Patent number
US08288397B2

Reaction notes

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