Hydrochloric Acid → 3-(3-Oxo-3-phenyl-1-propenyl)-benzoic acid

HRID 1647227Notes

Reaction equation

HRID 1647227 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=O.[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[CH3:13].[OH-].[Na+].Cl>C(O)C.O>[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:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 120773-CarboxybenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 540286713-(3-Oxo-3-phenyl-1-propenyl)-benzoic acidYield 84.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 3-formylbenzoic acid (2 g, 13.32 mmol), acetophenone (1.6 g, 13.32 mmol), and sodium hydroxide (1.06 g, 26.64 mmol) is stirred 18 hours in ethanol-water (175 mL, 1:1) and then acidified with concentrated hydrochloric acid. The resulting solid is collected by filtration and dried to provide 2.84 g of the title compound; mp 198°-201° C.

Workup

  1. filtrationThe resulting solid is collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-d25eeba8162d47098888e116c3e85b95
Source dataset
uspto-grants-1995_07
Patent number
US05430047

Reaction notes

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