Hydrochloric Acid → 4-(2-Carboxyethyl)benzalacetophenone

HRID 328922Notes

Reaction equation

HRID 328922 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=O.[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])[CH3:15].C(O)C.Cl>[OH-].[Na+]>[C:9]([CH2:8][CH2:7][C:6]1[CH:12]=[CH:13][C:3]([CH:1]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:4][CH:5]=1)([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7410AcetophenoneHCID 198252413-(4-Formylphenyl)propanoic acid

Product 1

HCID 543866524-(2-Carboxyethyl)benzalacetophenoneYield 100%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 5.34 g of 4-formyldihydrocinnamic acid in 50 ml of 1N sodium hydroxide was added a solution of 3.6 g of acetophenone and 20 ml of ethanol. The reaction mixture was stirred at room temperature for 4 hrs. and then poured onto 300 g of crushed ice. 1N Hydrochloric acid was added and, after stirring at 0° C for 15 min., the precipitate was collected and washed with water. The precipitate was dissolved in 500 ml of ethyl acetate, dried over anhydrous sodium sulfate and the drying agent was collected on a filter. The filtrate was concentrated to about 100 ml and seeded with crystalline product. The solid was collected, washed with 1:4-ethyl acetate-ether followed by ether and dried at 70°-75° C under vacuum to give 8.4 g (72%) of 4-(2-carboxyethyl)benzalacetophenone, as yellow needles, m.p. 159°-160° C.

Workup

  1. stirringafter stirring at 0° C for 15 min.
  2. customthe precipitate was collected
  3. washwashed with water
  4. dissolutionThe precipitate was dissolved in 500 ml of ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe drying agent was collected on a filter
  7. concentrationThe filtrate was concentrated to about 100 ml
  8. customThe solid was collected
  9. washwashed with 1
  10. customdried at 70°-75° C under vacuum

Sources & evidence

ORD record
ord-8ffc4ecec4f142dbbf54f60e10477700
Source dataset
uspto-grants-1977_04
Patent number
US04018884

Reaction notes

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