Hydrochloric Acid → 4-(4-Ethylphenyl)-4-oxobutanoic acid

HRID 2886

Reaction equation

HRID 2886 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:13]1(=[O:19])[O:18][C:16](=[O:17])[CH2:15][CH2:14]1.Cl>>[O:19]=[C:13]([C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)[CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7500EthylbenzeneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3169834-(4-Ethylphenyl)-4-oxobutanoic acid

Procedure

5 cm3 of ethylbenzene and 2.6 g of aluminum chloride are mixed with magnetic stirring in a 50-cm3 flask. The solution is cooled in an ice bath and 1 g of succinic anhydride is then added. The reaction mixture is stirred for 1 h 30 min at a temperature of 0° C. and then for 3 h at room temperature. It is poured into ice. The resulting mixture is acidified by adding 1N hydrochloric acid (pH 3-4). It is extracted with 3 volumes of ether. The organic phases are washed 3 times with 10% potassium carbonate solution. The aqueous phases are combined and acidified by adding concentrated hydrochloric acid. The precipitate obtained is drained and then recrystallized.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. stirringThe reaction mixture is stirred for 1 h 30 min at a temperature of 0° C.
  3. additionIt is poured into ice
  4. extractionIt is extracted with 3 volumes of ether
  5. washThe organic phases are washed 3 times with 10% potassium carbonate solution
  6. additionby adding concentrated hydrochloric acid
  7. customThe precipitate obtained
  8. customrecrystallized

Sources & evidence

ORD record
ord-14978e6518ec43e492e5f892cd564bb7
Source dataset
uspto-grants-1998_03
Patent number
US05731352

Linked notes

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