4-Acetylbenzoic Acid → HCID 10311637, compound

HRID 10688Notes

Reaction equation

HRID 10688 reaction equation
[CH3:1][O:2][C:3]1[C:10]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][C:6]([CH:7]=O)=[C:5]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[CH:4]=1.[C:27]([C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1)(=[O:29])[CH3:28]>>[CH3:1][O:2][C:3]1[C:10]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][C:6](/[CH:7]=[CH:28]/[C:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=2)=[O:29])=[C:5]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[CH:4]=1

Participants

3

Reactant 2

HCID 114704-Acetylbenzoic AcidHCID 161157614-Methoxy-2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-5-thiophen-2-yl-benzaldehyde

Product 1

HCID 10311637HCID 10311637, compoundYield 82%

Procedure

The title compound was prepared by condensing 4-methoxy-2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-5-thiophen-2-yl-benzaldehyde (Ex-68B) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 137–138° C., 82% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.20–8.23 (m, 3H), 8.09 (d, 2H, J=8.3 Hz), 8.01 (m, 2H), 7.66 (d, 1H, J=3.6 Hz), 7.52 (d, 1H, J=5.1 Hz), 7.13 (dd, 1H, J=5.1, 3.6 Hz), 6.88 (s, 1H), 4.37 (t, 2H, J=3.6 Hz), 4.01 (s, 3H), 3.89 (t, 2H, J=3.6 Hz), 3.64–3.67 (m, 2H), 3.53–3.56 (m, 2H), 3.47–3.50 (m, 2H), 3.36–3.95 (m, 2H), 3.19 (s, 3H). MS (ESI) m/z=527 ([M+H]+, 100%). Anal. Calcd. for C28H30O8S: C, 63.86; H, 5.74; S, 6.09. Found: C, 64.08; H, 5.77; S, 6.09.

Sources & evidence

ORD record
ord-6dfba431f171450685223b10c4f9e620
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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