Chlorobenzene → Ethyl 3-phenylprop-2-enoate

HRID 1194568Notes

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].Cl[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH:3][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 7964Chlorobenzene

HCID 8821Ethyl Acrylate

Product 1

HCID 7649Ethyl 3-phenylprop-2-enoate

Procedure

More specifically, we have found that chlorobenzene reacts with ethyl acrylate to form ethyl cinnamate in relatively high yield by reacting the chlorobenzene with iodide and/or bromide ion to form a mixture of chlorobenzene, iodobenzene and/or bromobenzene, then reacting the mixture with ethyl acrylate in the presence of a catalyst to form ethyl cinnamate.

Sources & evidence

ORD record: ord-9415efef69eb4afd9b01b0b7016c6600
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04814489

Reaction notes

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