4-Formylbenzoic acid → Methyl 4-carboxycinnamate

HRID 564919Notes

Reaction equation

HRID 564919 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.[CH3:12][O:13][C:14](=[O:35])[CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:7]([C:6]1[CH:10]=[CH:11][C:3]([CH:1]=[CH:15][C:14]([O:13][CH3:12])=[O:35])=[CH:4][CH:5]=1)([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 54440358Methyl 4-carboxycinnamateYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-formylbenzoic acid (1.00 g) in dry tetrahydrofuran (15 ml) was added methyl(triphenylphosphoranylidene)acetate (2.50 g) at ambient temperature under nitrogen atmosphere. The reaction mixture was stirred for 1 hour at the same temperature, poured into aqueous sodium bicarbonate solution, and washed with ethyl acetate. 1N-Hydrochloric acid was added to the aqueous layer until the layer was adjusted to pH 2. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give methyl 4-carboxycinnamate (1.21 g) as colorless powder.

Workup

  1. washwashed with ethyl acetate
  2. addition1N-Hydrochloric acid was added to the aqueous layer until the layer
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-a6f36ede9ed74b8c8d2ea39a57c24c78
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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