1-(4-Chloronaphthalen-1-yl)ethanone → 4-Chloronaphthalene-1-carboxylic acid

HRID 1289769Notes

Reaction equation

HRID 1289769 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([Cl:14])=[CH:6][CH:5]=1)(=[O:3])C.Cl[O-:16].[Na+]>Cl>[Cl:14][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([C:1]([OH:3])=[O:16])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 125518731-(4-Chloronaphthalen-1-yl)ethanoneHCID 23665760Sodium Hypochlorite

Product 1

HCID 127491434-Chloronaphthalene-1-carboxylic acidYield 23%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The compound (8.33 g) obtained in (1) above and a 5% sodium hypochlorite solution (380 ml) were stirred with refluxing for 44 hours. The reaction mixture was cooled to room temperature and concentrated hydrochloric acid (10 ml) was dropwise added. The resulting solid was collected by filtration. The obtained solid was subjected to silica gel column chromatography (hexane-ethyl acetate) to give 1.96 g of a red-brown solid (yield 23%).

Workup

  1. temperaturewith refluxing for 44 hours
  2. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-4e26f66d41f145f9a6cccea0b4ab956c
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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