Acrylic Acid → Acrylic anhydride

HRID 2396399Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=CC=CC=1.[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12]>>[C:10]([O:14][C:1](=[O:8])[CH:2]=[CH2:7])(=[O:13])[CH:11]=[CH2:12]

Participants

Reactant 2

HCID 6581Acrylic Acid

HCID 7412Benzoyl chloride2×

Product 1

HCID 74919Acrylic anhydride

Procedure

Moreover, in the case of benzoyl chloride, the resulting mixed anhydride is more reactive than benzoyl chloride. Thus, the carboxylate ion of acrylic acid preferentially reacts with the mixed anhydride to give acrylic anhydride and the benzoate ion, which subsequently reacts with unreacted benzoyl chloride to give benzoic anhydride, according to reaction scheme I.

Sources & evidence

ORD record: ord-956688a6dc2a418baaac869d385ba646
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491244

Reaction notes

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