3-Acetylbenzoic acid → 3-[3E-(2,4-Dimethoxy-5-thiophen-2-yl-phenyl)-acryloyl]-benzoic acid

HRID 10657Notes

Reaction equation

HRID 10657 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][C:4]=1[CH:5]=O.[C:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([OH:26])=[O:25])(=[O:20])[CH3:19]>>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][C:4]=1/[CH:5]=[CH:19]/[C:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([OH:26])=[O:25])=[O:20]

Participants

3

Reactant 2

HCID 2203243-Acetylbenzoic acidHCID 161161832,4-Dimethoxy-5-thien-2-ylbenzaldehyde

Product 1

HCID 101506813-[3E-(2,4-Dimethoxy-5-thiophen-2-yl-phenyl)-acryloyl]-benzoic acidYield 65%

Procedure

The title compound was prepared by condensing 2,4-dimethoxy-5-(thiophen-2-yl)-benzaldehyde (Ex-6A) and 3-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 65% yield, mp 179–182° C. 1H-NMR (DMSO-d6) δ 8.54 (s, 1H), 8.39 (d, 1H), 8.25 (s, 1H), 8.15 (d, 1H), 8.04 (d, 1H), 7.90 (d, 1H), 7.67 (m, 2H), 7.48 (d, 1H), 7.09 (t, 1H), 6.81 (s, 1H), 3.98 (s, 3H), 3.97 (s, 3H). MS m/z=394 ([M]+, 72%), 363 (100%). Anal. calculated for C22H18O5S: C, 66.99; H, 4.60; S, 8.13; found C, 66.80; H, 4.60; S, 8.07.

Sources & evidence

ORD record
ord-e3bb6c43f89f4a48b1f3998f4095d6e4
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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