4-Acetylbenzoic Acid → 4-[3E-(3-Thiophen-2-yl-phenyl)-acryloyl]-benzoic acid

HRID 10656

Reaction equation

HRID 10656 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O.[C:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)(=[O:16])[CH3:15]>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8](/[CH:9]=[CH:15]/[C:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)=[O:16])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 114704-Acetylbenzoic AcidHCID 42811003-(2-Thienyl)benzaldehyde

Product 1

HCID 101499014-[3E-(3-Thiophen-2-yl-phenyl)-acryloyl]-benzoic acidYield 71%

Procedure

The title compound was prepared by condensing 3-(thiophen-2-yl)-benzaldehyde (Ex-42A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 238° C. (dec), 71% yield. 1H-NMR (DMSO-D6) δ 13.40 (bs, 1H), 8.29 (d, J=8 Hz, 2H), 8.22 (s, 1H), 8.13 (d, J=8 Hz, 2H), 8.04 (s, 1H), 7.87 (s, 1H), 7.83 (d, J=8 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 7.69 (d, J=4 Hz, 1H), 7.63 (d, J=5 Hz, 1H), 7.52 (t, J=8 Hz, 1H), 7,20 (dd, J=4, 5 Hz, 1H). HRMS m/z=calc. 335.0742, found 335.0749.

Sources & evidence

ORD record
ord-12ec378e0f82417390911f19266aae37
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

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