Benzaldehyde → 3-Phenylprop-2-enoyl chloride

HRID 1368008Notes

Reaction equation

HRID 1368008 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

FIG. 1 shows the synthesis of a cellulose cinnamate according to an embodiment of the present invention. 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 CelCN is finally synthesized by reacting cellulose, or cellulose acetate, 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 CelCN is obtained.

Sources & evidence

ORD record
ord-5dc7bba665ae446cb1cc9c267fd66fac
Source dataset
uspto-grants-2003_06
Patent number
US06572939B2

Reaction notes

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