2-Naphthoic acid → 2-Naphthoyl chloride

HRID 1107891Notes

Reaction equation

HRID 1107891 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-73c299068fc347e1930ffb4d5f311b29
Source dataset
uspto-grants-2000_05
Patent number
US06063800

Reaction notes

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