Hydrochloric Acid → 4-Carboxychalcone

HRID 1180811Notes

Reaction equation

HRID 1180811 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[CH3:13].[OH-].[Na+].Cl>CO>[O:14]=[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:13]=[CH:1][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7410Acetophenone2×HCID 120884-Formylbenzoic acidHCID 14798Sodium Hydroxide

Product 1

HCID 39957814-CarboxychalconeYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension at room temperature of 4-formylbenzoic acid (2.58 g, 17 mmol) and acetophenone (2.0 ml, 17 mmol) or acetophenone derivatives (1.0–1.1 equiv.) in MeOH (100 ml) was added a solution of NaOH (34 ml, 1N in H2O). After 16 h, the reaction mixture was acidified with conc. HCl (pH=1–2), filtered off, rinsed with H2O and dried to afford the title compound XXIIIa (3.73 g, 14.6 mmol, 86% yield) as a yellow solid.

Workup

  1. filtrationfiltered off
  2. washrinsed with H2O
  3. customdried

Sources & evidence

ORD record
ord-a1f470d23b0e4bd192d5e823facbd413
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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