Hydrochloric Acid → 4-Carboxychalcone

HRID 1923464Notes

Reaction equation

HRID 1923464 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[C:12]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)([OH:14])=[O:13].Cl>O.C(O)C>[O:5]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:4]=[CH:19][C:18]1[CH:21]=[CH:22][C:15]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1

Participants

7

Reactant 4

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

Product 1

HCID 39957814-CarboxychalconeYield 38.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydroxide (128.0 g, 3.2 mol) is dissolved in water (1400 mL) and ethanol (675 mL). The mixture is cooled to 20° C. and acetophenone (120 g, 0.5 mol) is added with mechanical stirring. 4-Carboxybenzaldehyde (75 g, 0.5 mol) and the reaction stirred at room temperature for 6 h. The reaction is acidified with concentrated HCl (300 mL) and extracted with ethyl acetate (3×). The combined organic portions are washed with water, saturated brine, dried, and evaporated in vacuo. The material is recrystallized from isopropanol with a small amount of methanol to obtain 48 g (38%) of the titled compound. m.p.=197-200° C.; Anal. Calcd for C16H12O3: C, 76.18; H, 4.79. Found: C, 76.03; H, 5.05.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic portions are washed with water, saturated brine
  3. customdried
  4. customevaporated in vacuo
  5. customThe material is recrystallized from isopropanol with a small amount of methanol

Sources & evidence

ORD record
ord-24294f9644654cbe8ce6af8fe5e67ead
Source dataset
uspto-grants-2012_05
Patent number
US08178528B2

Reaction notes

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