Naphthalene → 4-(2-Naphthyl)-4-oxobutanoic acid

HRID 639761Notes

Reaction equation

HRID 639761 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-]>ClC(Cl)C.O.Cl>[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

7

Reactant 3

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

Product 1

HCID 2200044-(2-Naphthyl)-4-oxobutanoic acidYield 41.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Naphthalene (5.0 gm, 0.039 moles) and succinic anhydride (4.68 gm, 0.0468 moles) were taken up in dichloroethane (50 ml). Aluminium chloride (11.44 g, 0.0858 moles) was added at room temperature and the resulting mixture heated under reflux for 1 hr with stirring. The reaction mixture was cooled to room temperature, diluted with 25 ml of 1:1 mixture of water and Conc. hydrochloric acid. After stirring for 10 min the separated solid was filtered under suction, washed with water and dilute hydrochloric acid. Subsequent column chromatography gave a buff coloured solid. Subsequent chromatography gave 3.7 gm (41%) the title compound, mp 173-174° C.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 1 hr
  3. stirringAfter stirring for 10 min the separated solid
  4. filtrationwas filtered under suction
  5. washwashed with water and dilute hydrochloric acid
  6. customSubsequent column chromatography gave a buff

Sources & evidence

ORD record
ord-6e7b97be8d384eacaeeacca05e0e7e63
Source dataset
uspto-grants-2010_04
Patent number
US07691889B2

Reaction notes

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