2-Naphthoic acid → 2-Naphthoyl chloride

HRID 619338Notes

Reaction equation

HRID 619338 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.S(Cl)([Cl:16])=O>ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([Cl:16])=[O:13]

Participants

4

Reactant 2

HCID 71232-Naphthoic acidHCID 24386Thionyl Chloride

Product 1

HCID 752462-Naphthoyl chlorideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-naphthyl carboxylic acid (76.5 g, 0.45 mol) in dichloromethane (500 ml) was added thionyl chloride (38.7 ml, 0.53 mol) and the mixture was heated at reflux temperature for 48 h. The volatiles were evaporated in vacuo affording 80 g (94%) of 2-naphthoyl chloride.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 48 h
  3. customThe volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-465155aeefbd46708ad9673ef0c6b50a
Source dataset
uspto-grants-1999_09
Patent number
US05958957

Reaction notes

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