Hydrochloric Acid → 4-Carboxychalcone

HRID 328927Notes

Reaction equation

HRID 328927 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)([OH:5])=[O:4].[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])[CH3:15].Cl>O.C(O)C>[C:3]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:8][CH:7]=1)([OH:5])=[O:4]

Participants

7

Reactant 4

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

Product 1

HCID 39957814-CarboxychalconeYield 61.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.0 g of sodium hydroxide in 25 ml of water and 10 ml of ethanol was added 4.50 g of 4-carboxybenzaldehyde (supplied by the Aldrich Chemical Company, Milwaukee, Wis.) in one portion. After stirring for 15 min. at room temperature, 3.60 g of acetophenone was added and the resulting solution was stirred at room temperature for 3 hrs. The reaction mixture was cooled in an ice-bath and acidified with 75 ml of 1N hydrochloric acid. The precipitate was collected, washed with water and air-dried. Recrystallization from methanol gave 4.64 g (61%) of 4-carboxybenzalacetophenone as yellow crystals, m.p. 227°-229° C after drying at 90°-95° C under vacuum for 4 hrs.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 3 hrs
  2. temperatureThe reaction mixture was cooled in an ice-bath
  3. customThe precipitate was collected
  4. washwashed with water
  5. customair-dried
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-76f2c05450f9433089b1224098b68980
Source dataset
uspto-grants-1977_04
Patent number
US04018884

Reaction notes

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