4-Acetylbenzoic Acid → 4-[3E-(3-Benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzoic acid

HRID 10659Notes

Reaction equation

HRID 10659 reaction equation
[S:1]1[C:5]([C:6]2[C:7]([O:16][CH3:17])=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[CH:9]=O)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2.[C:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1)(=[O:24])[CH3:23]>>[S:1]1[C:5]([C:6]2[C:7]([O:16][CH3:17])=[C:8](/[CH:9]=[CH:23]/[C:22]([C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)=[O:24])[CH:11]=[CH:12][C:13]=2[O:14][CH3:15])=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2

Participants

3

Reactant 2

HCID 114704-Acetylbenzoic AcidHCID 21981050HCID 21981050, compound

Product 1

HCID 101514534-[3E-(3-Benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzoic acidYield 64%

Procedure

The title compound was prepared by condensing 3-benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde (Ex-44B) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 237° C. (dec.), 64% yield. 1H-NMR (DMSO-d6) δ 13.37 (bs, 1H), 8.20–8.25 (m, 3H), 8.11 (d, J=8 Hz, 2H), 8.02 (d, J=8 Hz, 1H), 7.96 (d, J=9 Hz, 2H), 7.88–7.91 (m, 1H), 7.65 (s, 1H), 7.35–7.43 (m, 2H), 7.14 (d, J=9 Hz, 1H), 3.90 (s, 3H), 3.53 (s, 3H). HRMS m/z=calc. 445.1110, found 445.1112.

Sources & evidence

ORD record
ord-b003aa407c8c4f929c308d4ff24f7600
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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