Hydrochloric Acid → 1-(4-Chloronaphthalen-1-yl)ethanone

HRID 1289768Notes

Reaction equation

HRID 1289768 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[C:16](Cl)(=[O:18])[CH3:17].Cl>ClCCl>[C:16]([C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([Cl:5])=[CH:7][CH:8]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 70031-ChloronaphthaleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125518731-(4-Chloronaphthalen-1-yl)ethanoneYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To aluminum chloride (54.5 g) and dichloromethane (250 ml) was dropwise added 1-chloronaphthalene (47 ml) under ice-cooling over 10 minutes. The obtained reaction mixture was stirred for 20 minutes and acetyl chloride (25 ml) was dropwise added over 40 minutes. The reaction mixture was stirred at room temperature for 4 hours and with refluxing for 20 minutes. The reaction mixture was cooled to room temperature, poured into 1N hydrochloric acid (300 ml), extracted with dichloromethane, washed with saturated brine and dried over magnesium sulfate. The solvent was distilled away and the residue was subjected to silica gel column chromatography (hexane-ethyl acetate) to give 37.3 g of a red-brown liquid (yield 55%).

Workup

  1. temperaturecooling over 10 minutes
  2. customThe obtained reaction mixture
  3. stirringThe reaction mixture was stirred at room temperature for 4 hours
  4. temperaturewith refluxing for 20 minutes
  5. extractionextracted with dichloromethane
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-393b1f0a7d6c42d3be530311993045b7
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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