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

HRID 10644Notes

Reaction equation

HRID 10644 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:4]=1.[C:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)(=[O:18])[CH3:17]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:17]/[C:16]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)=[O:18])=[C:5]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 114704-Acetylbenzoic AcidHCID 21981110HCID 21981110, compound

Product 1

HCID 210416234-[3E-(4-Methoxy-2-thiophen-2-yl-phenyl)-acryloyl]-benzoic acidYield 61%

Procedure

The title compound was prepared by condensing 4-methoxy-2-thiophen-2-yl-benzaldehyde (Ex-34A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, 61% yield, m.p. 209–211° C. 1H-NMR (300 MHz, d6-DMSO): 8.14 (m, 3H), 8.04 (d, 2H, J=9.2 Hz), 7.89 (d, 1H, J=15.5 Hz), 7.76 (d, 1H, J=15.5 Hz), 7.70 (d, 1H, J=5.0 Hz), 7.18 (dd, 1H, J=5.6 and 3.6 Hz), 7.11 (d, 1H, J=2.1 Hz), 7.05 (dd, 1H, J=8.8 and 1.8 Hz), 6.98 (d, 1H, J=1.8 Hz), 3.83 (s, 3H). MS m/z=364 ([M]+, 100%). HRMS (EI) Calcd. for C21H16O4S: 364.0769. Found: 364.0761.

Sources & evidence

ORD record
ord-ff54610c7ba349f89734c05c02f5bd56
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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