Acetic Anhydride → 3-(2,4-Difluorophenyl)acrylic Acid

HRID 130603

Reaction equation

[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:14]C(=O)C)(=[O:13])[CH3:12]>>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:12][C:11]([OH:14])=[O:13]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 6035023-(2,4-Difluorophenyl)acrylic AcidYield 77%

Procedure

A disadvantage here is the high reaction temperature needed, the unsatisfactory yield and the difficult accessibility of the compounds of the formula (I). Monatshefte der Chemie 90, 680 (1959) describes the reaction of 2,4-difluorobenzaldehyde with acetic anhydride at 180° C., 2,4-difluoro-cinnamic acid being obtained in a 77% yield.

Workup

customthe unsatisfactory yield

Sources & evidence

ORD record: ord-713f7e8e136d41799a23ae377085f383
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381832B2

Linked notes

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