4-Formylbenzoic acid → Methyl 4-carboxycinnamate

HRID 726290Notes

Reaction equation

HRID 726290 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-cc8d013df04343c08dfccf79b1251f56
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

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