Acetyl chloride → 1-(5-Chloro-6-methoxynaphthalen-2-yl)ethan-1-one

HRID 268337Notes

Reaction equation

HRID 268337 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[C:14](Cl)(=[O:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[C:14]([C:8]1[CH:9]=[CH:10][C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:12][CH3:13])[C:2]=2[Cl:1])[CH:7]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 115646231-Chloro-2-methoxynaphthalene

Product 1

HCID 158904591-(5-Chloro-6-methoxynaphthalen-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A mixture of 1925 g. of 1-chloro-2-methoxynaphthalene, 80 g. of acetyl chloride, 400 g. of aluminum chloride and 2.5 liters of nitrobenzene are stirred for 60 hours at room temperature. The resulting mixture is then washed with dilute hydrochloric acid, dried over sodium sulfate and evaporated to yield 2-acetyl-5-chloro-6-methoxynaphthalene. The resulting acetyl product is added to a mixture of 39 g. of sulfur and 105 g. of morpholine and heated to about 150° C for 3 hours. The mixture is then added to 1 liter of concentrated hydrochloric acid and refluxed for 3 hours. The mixture is then cooled, diluted with 6 liters of ice-water and extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate and evaporated to yield 2-(5'-chloro-6'-methoxy-2'-naphthyl) acetic acid.

Workup

  1. additionA mixture of 1925 g
  2. washThe resulting mixture is then washed with dilute hydrochloric acid
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-32bd5ca0f0c841d2bd5fc93cc13a809a
Source dataset
uspto-grants-1976_03
Patent number
US03947472

Reaction notes

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