Chlorosuccinimide → 1-(4-Chloro-1-hydroxy-naphthalen-2-YL)-ethanone

HRID 1192543Notes

Reaction equation

HRID 1192543 reaction equation
[OH: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[C:12](=[O:14])[CH3:13].[Cl:15]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:15][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:12](=[O:14])[CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 697331'-Hydroxy-2'-acetonaphthone

Product 1

HCID 114814261-(4-Chloro-1-hydroxy-naphthalen-2-YL)-ethanoneYield 67.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 1-(1-hydroxy-2-naphthyl)ethanone (5.00 g, 26.8 mmol, from Aldrich) in acetic acid (100 mL) was added N-chlorosuccinimide (3.94 g, 29.5 mmol) and the resulting mixture heated at 100° C. for 18 hours. After allowing to be cooled to ambient temperature, the reaction mixture was concentrated in vacuo and then diluted with ethyl acetate. The precipitated solid was collected by filtration to afford the desired product (3.98 g, 67%). LCMS calculated for C12H10ClO2 (M+H)+: m/z=221.0; Found: 221.1.

Workup

  1. temperatureto be cooled to ambient temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-aa27fc8e005b4a8fb67e4c8e976c61fb
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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