4-Formylbenzoic acid → 4-((1E)-3-methoxy-3-oxoprop-1-en-1-yl)benzoic acid

HRID 220888Notes

Reaction equation

HRID 220888 reaction equation
[H-].[Na+].[CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=O.C1(P(=[CH:33][C:34]([O:36][CH3:37])=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:37][O:36][C:34](/[CH:33]=[CH:3]/[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:35]

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 24758Sodium hydride

Product 1

HCID 106083304-((1E)-3-methoxy-3-oxoprop-1-en-1-yl)benzoic acidYield 53.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (60% dispersion in oil, 1.46 g, 36.6 mmol) was added to a solution of 4-formylbenzoic acid (5.0 g, 33.3 mmol) in toluene (200 ml) and the mixture was stirred for 2 h at room temperature. Methyl (triphenyl-phosphoranylidene)acetate (11.69 g, 35.0 mmol) was added and the mixture was heated at reflux for 20 h. Solvents were removed in vacuo and the residue was redissolved in dichloromethane and 1M NaHCO3. The layers were partitioned and the aqueous layer was acidified with 1M HCl solution then extracted with chloroform. The organic layer was dried and concentrated in vacuo to yield the title compound (3.65 g, 53%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 20 h
  3. customSolvents were removed in vacuo
  4. dissolutionthe residue was redissolved in dichloromethane
  5. customThe layers were partitioned
  6. extractionthen extracted with chloroform
  7. customThe organic layer was dried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f91059fe21ba42e3b176f973ee740d68
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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