Methanol → Methyl 4-ethynylbenzoate

HRID 1177939Notes

Reaction equation

HRID 1177939 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH:7]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)=O.[CH3:18][OH:19]>C(Cl)Cl>[CH3:18][O:19][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([C:7]#[CH:1])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 120884-Formylbenzoic acid

Product 1

HCID 640163Methyl 4-ethynylbenzoateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium carbonate (316 mg, 2.28 mmol) was added to a stirred solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl (400 mg, 2.08 mmol) and 4-formyl-benzoic acid (341 mg, 2.08 mmol) in MeOH (20 mL) and continued stirring at room temperature overnight. The reaction mixture was filtered and concentrated to get the residue. The residue obtained was diluted with DCM and organic phase was washed with 5% sodium bicarbonate and brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 310 mg (79.4% yield) 4-ethynyl-benzoic acid methyl ester.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto get the residue
  4. customThe residue obtained
  5. washwas washed with 5% sodium bicarbonate and brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ebe3018c25cd4443a7131428c1b1f168
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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