Hydrochloric Acid → 4-(2-Naphthyl)-4-oxobutanoic acid

HRID 329348Notes

Reaction equation

HRID 329348 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][C:8]=1[C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 931NaphthaleneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2200044-(2-Naphthyl)-4-oxobutanoic acidYield 59.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 900 ml of dichloromethane contained in a 3 liter, 3-neck flask equipped with a mechanical stirrer, drying tube and thermometer and surrounded by an ice water bath was added 290.0 g (2.26 moles) naphthalene. To the stirred suspension was added 145.2 g (1.44 moles) of succinic anhydride. A total of 400 g of aluminum chloride was then added in small increments over the next 41/2 hours while stirring and cooling in an ice water bath. The resulting amber brown-yellow reaction mixture was stirred at room temperature overnight. Next morning it was poured on crushed ice and acidified with conc. hydrochloric acid. The aqueous portion was decanted and the organic layer was filtered to collect white solids. The solids were washed with dichloromethane containing 20% hexanes and slurried in 700 ml of boiling ethyl acetate. After cooling in a cold water bath, the solids were collected by filtration and washed with fresh ethyl acetate. Then the solids were recrystallized from 500 ml of glacial acetic acid and dried under vacuum to give 195.0 g (59.4% yield) of 4-(2-naphthyl)4-oxobutyric acid as an off-white solid. M.P. 171°-175° C.; M/e 229; λmax 282 nm (7,260) in ethanol.

Workup

  1. customequipped with a mechanical stirrer
  2. customdrying tube
  3. customthermometer and surrounded by an ice water bath
  4. temperaturecooling in an ice water bath
  5. stirringThe resulting amber brown-yellow reaction mixture was stirred at room temperature overnight
  6. additionNext morning it was poured
  7. customon crushed ice
  8. customThe aqueous portion was decanted
  9. filtrationthe organic layer was filtered
  10. customto collect white solids
  11. washThe solids were washed with dichloromethane containing 20% hexanes
  12. temperatureAfter cooling in a cold water bath
  13. filtrationthe solids were collected by filtration
  14. washwashed with fresh ethyl acetate
  15. customThen the solids were recrystallized from 500 ml of glacial acetic acid
  16. customdried under vacuum

Sources & evidence

ORD record
ord-c417be6891a745f1951d2a07ad137699
Source dataset
uspto-grants-1990_01
Patent number
US04891298

Reaction notes

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