Benzaldehyde → 2-Propenoic acid, 3-phenyl-

HRID 1862587Notes

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:12]C(=O)C)(=[O:11])[CH3:10]>>[C:9]([OH:12])(=[O:11])[CH:10]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 240Benzaldehyde

HCID 7918Acetic Anhydride

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 19%

Procedure

Kalnin, Helv. Chim. Acta 11, 977 (1928) describes various salts as catalysts. 1 mol of benzaldehyde and 1.5 mol of acetic anhydride are refluxed at 180° C. for 8 hours with 0.65 mol of catalyst. The yields of cinnamic acid are, following work-up, for potassium acetate 72%, for potassium carbonate 59%, for sodium carbonate 40%, for sodium acetate 39%, for sodium phosphate 36%, for potassium phosphate 20% and for potassium sulphide 32%. As well as potassium and sodium salts, amines are also possible as catalysts. For 0.33 mol of triethylamine, the yield is 19%.

Sources & evidence

ORD record: ord-a2521455ccd5493d857335da589203b2
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06538154B2

Reaction notes

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