Lithium hydroxide, monohydrate → 2-(2-Ethynylphenyl)acetic acid

HRID 1711082Notes

Reaction equation

HRID 1711082 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16]C)=[O:15])(C)C.C1COCC1.CO.O.[OH-].[Li+]>O>[C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([OH:16])=[O:15])#[CH:5]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 59457733Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate

Product 1

HCID 587728652-(2-Ethynylphenyl)acetic acidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ester 319 (4.65 g, 18.9 mmol) in 1:1 THF/methanol (100 mL) was added lithium hydroxide monohydrate (1.60 g, 38.1 mmol) in water (25 mL) and the mixture was stirred at r.t. for 30 min. It was then partially concentrated, the aqueous residue was washed with ether, then acidified with 3M HCl (aq) and extracted with ethyl acetate. The organic extract was washed with water, dried (anhydrous MgSO4), filtered and concentrated. The residue was dissolved in ethyl acetate, run through a short plug of silica gel, and concentrated to provide 320 (2.77 g, 92% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.40 (br s, 1H); 7.45 (d, J=8.0 Hz, 1H), 7.37-7.24 (m, 3H), 4.36 (s, 1H); 3.72 (s, 2H). LCMS: (M+Na) 183.1

Workup

  1. concentrationIt was then partially concentrated
  2. washthe aqueous residue was washed with ether
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-265f8844a5c5417c9ee993bbde413302
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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