Water → 4-Ethynylbenzoic acid

HRID 1177940

Reaction equation

HRID 1177940 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[CH:13])=[CH:8][CH:7]=1.O>CO.O>[C:12]([C:9]1[CH:10]=[CH:11][C:6]([C:5]([OH:14])=[O:4])=[CH:7][CH:8]=1)#[CH:13]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 640163Methyl 4-ethynylbenzoate

Product 1

HCID 5897064-Ethynylbenzoic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

LiOH (95.97 mg, 2.2 mmol) was added to a stirred solution of 4-ethynyl-benzoic acid methyl ester (305 mg, 1.9 mmol) in MeOH:H2O (1:1, 6 mL), and the resulting mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added, acidified it with conc.HCl and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 226 mg (81.9% yield) of 4-ethynyl-benzoic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get the residue
  3. extractionHCl and extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7dcc3f786f9d404a9c76c6f619b43ad7
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Linked notes

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