Hydrochloric Acid → (E)-4-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)benzoic acid

HRID 884648Notes

Reaction equation

HRID 884648 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.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][C:14]=1[CH3:22].[OH-].[K+].Cl>CO.O>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])/[CH:20]=[CH:1]/[C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=2)=[CH:15][C:14]=1[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 120884-Formylbenzoic acidHCID 14797Potassium HydroxideHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 57831176(E)-4-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)benzoic acidYield 88.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Commercially available 4-formylbenzoic acid (15.0 g, 0.1 mol) and commercially available 4′-hydroxy-3′-methylacetophenone (15.0 g, 0.1 mol) were dissolved in 150 mL of methanol and 50 mL of water. The solution was cooled with an ice-water bath, to which was added potassium hydroxide (28.0 g, 0.5 mol). The reaction mixture was stirred overnight. The resulted mixture was poured on to 600 mL of ice-water, acidified to pH=4-5 with 1 M HCl, filtered, washed with water (200 mL), and dried in the air. 25 g (87%) of a yellowish solid was obtained.

Workup

  1. temperatureThe solution was cooled with an ice-water bath, to which
  2. filtrationfiltered
  3. washwashed with water (200 mL)
  4. customdried in the air

Sources & evidence

ORD record
ord-e92557d2fc8148fe846576ecf620b9cd
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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