Benzaldehyde → 3-Phenylprop-2-enoyl chloride

HRID 1370149Notes

Reaction equation

HRID 1370149 reaction equation
[C:1]([OH:11])(=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)C1C=CC=CC=1.C(O)(=O)CC(O)=O.S(Cl)([Cl:29])=O>N1C=CC=CC=1.N1CCCCC1>[C:1]([Cl:29])(=[O:11])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 867Malonic AcidHCID 87842-Propenoic acid, 3-phenyl-2×HCID 24386Thionyl Chloride

Product 1

HCID 660233-Phenylprop-2-enoyl chloride

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8082PiperidineSolvent

Procedure

A cinnamic acid is first prepared by reacting a benzaldehyde with malonic acid in pyridine and piperidine. The cinnamic acid is then reacted with thionyl chloride to produce a cinnamoyl chloride derivative. The PECN is finally synthesized by reacting PECN with the cinnamoyl chloride derivative in an inert solvent (such as chloroform, nitrobenzene, chlorobenzene, or the like). The reaction mixture is diluted with methanol, filtered, dried in a vacuum, and milled by a vibrating mill, whereupon the PECN is obtained.

Sources & evidence

ORD record
ord-03ea329e33e94aeaba73c8cae8e8eb81
Source dataset
uspto-grants-2003_06
Patent number
US06582784B2

Reaction notes

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