Hydrochloric Acid → 4-(1-Naphthyl)-4-oxobutanoic acid

HRID 1501

Reaction equation

HRID 1501 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-].[Cl-].[Cl-].[Al+3].Cl>[N+](C1C=CC=CC=1)([O-])=O>[C:9]1([C:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:17])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

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

Product 1

HCID 2777864-(1-Naphthyl)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A mixture of naphthalene (40 g) and succinic anhydride (20 g) was added to a well stirred suspension of aluminum trichloride (55 g) in nitrobenzene (140 ml). The resulting mixture was stirred overnight at room temperature. The mixture was then poured slowly onto ice-water (600 g) and acidified with 6N-hydrochloric acid. The crude acid was filtered, washed with water until washings were neutral and recrystallized from ethanol yielding the product (m.p. 170°-172° C.).

Workup

  1. additionwas added to a well
  2. stirringThe resulting mixture was stirred overnight at room temperature
  3. additionThe mixture was then poured slowly onto ice-water (600 g)
  4. filtrationThe crude acid was filtered
  5. washwashed with water until washings
  6. customrecrystallized from ethanol yielding the product (m.p. 170°-172° C.)

Sources & evidence

ORD record
ord-d1ffe8aa63584752873a03df8fe427f6
Source dataset
uspto-grants-1998_03
Patent number
US05726162

Linked notes

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