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4-Acetylbenzoic Acid → 4-[3-(5-benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-E-acryloyl]-benzoic acid

HRID 10620
Notes
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Reaction equation

HRID 10620 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[S:13]1[C:17]([C:18]2[C:19]([O:28][CH3:29])=[CH:20][C:21]([O:26][CH3:27])=[C:22]([CH:25]=2)[CH:23]=O)=[CH:16][C:15]2[CH:30]=[CH:31][CH:32]=[CH:33][C:14]1=2.[OH-].[Na+]>CN(C)C=O.O>[S:13]1[C:17]([C:18]2[C:19]([O:28][CH3:29])=[CH:20][C:21]([O:26][CH3:27])=[C:22](/[CH:23]=[CH:2]/[C:1]([C:4]3[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=3)=[O:3])[CH:25]=2)=[CH:16][C:15]2[CH:30]=[CH:31][CH:32]=[CH:33][C:14]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 114704-Acetylbenzoic AcidHCID 14798Sodium HydroxideHCID 161159165-Benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde

Product 1

HCID 99331504-[3-(5-benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-E-acryloyl]-benzoic acidYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 4-acetylbenzoic acid (1.50 g, 9.1 mmol) and 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde from Ex-3A (3.27 g, 11.0 mmol) in N,N-dimethylformamide (76 mL) was added a solution of sodium hydroxide (5 M, 7.3 mL, 36.5 mmol). The reaction mixture was allowed to stir at room temperature for 2 h and was then diluted with water to a volume of 150 mL. The solution was washed with dichloromethane and acidified with concentrated sulfuric acid to pH=3. The resulting solution was then extracted with dichloromethane. The dichloromethane extract was washed with brine, dried over sodium sulfate and concentrated. The resulting oily product solidified in ethanol. The solid was further stirred in ethanol for one day and collected by filtration. The solid was washed with ethanol, then dried in vacuo to afford the title compound as a yellow solid (2.2 g, 54%). 1H NMR (300 MHz, DMSO-d6) δ 8.36 (s, 1H), 8.21 (d, 2H), 8.07 (m, 3H), 7.93 (m, 3H), 7.82 (d, 1H), 7.32 (m, 2H), 6.86 (s, 1H), 4.08 (s, 3H), 4.00 (s, 3H). Anal. Calculated for C26H20O5S·1/6H2O: C, 69.78; H, 4.58; S, 7.17; found: C, 69.95; H, 4.69; S, 7.15. HPLC purity: 97.9% (area percentage).

Workup

  1. washThe solution was washed with dichloromethane
  2. extractionThe resulting solution was then extracted with dichloromethane
  3. extractionThe dichloromethane extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. stirringThe solid was further stirred in ethanol for one day
  8. filtrationcollected by filtration
  9. washThe solid was washed with ethanol
  10. customdried in vacuo

Sources & evidence

ORD record
ord-80ec1d096bde430b80ffb02cef23687a
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094801B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes