4-Acetylbenzoic Acid → HCID 68977704, compound

HRID 1180796Notes

Reaction equation

HRID 1180796 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].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH:17]=O.[OH-].[Na+]>CO>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:2][C:1]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)=[O:3])[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

5

Reactant 3

HCID 114704-Acetylbenzoic AcidHCID 14798Sodium HydroxideHCID 227103,4-Dichlorobenzaldehyde

Product 1

HCID 68977704HCID 68977704, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension at room temperature of 4-acetylbenzoic acid (1.71 g, 10.44 mmol), 3,4-dichlorobenzaldehyde (2.05 g, 11.49 mmol) or aldehyde (1.1 equiv.) in MeOH (50 ml) was added a solution of NaOH (26.1 ml, 1N in H2O). After 19 h, the reaction mixture was filtered off, rinsed with MeOH and dried to afford the title compound IIa (3.22 g, 10.03 mmol, 96% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ(ppm): 8.35 (s, 1H), AB system (δA=8.13, δB=8.01, J=8.4 Hz, 4H), 8.12 (d, J=15.8 Hz, 1H), 7.93 (d, J=7.9 Hz, 1H), 7.76 (d, J=8.3 Hz, 1H, 7.73 (d, 15.8 Hz, 1H).

Workup

  1. filtrationthe reaction mixture was filtered off
  2. washrinsed with MeOH
  3. customdried

Sources & evidence

ORD record
ord-5dca1a21f94b421bb06c8a2b7ec56ae7
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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