2-Naphthoic acid → 2-Naphthoyl chloride

HRID 1741149Notes

Reaction equation

HRID 1741149 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-2ce798ec355f4c18b40b8b2deebf15ed
Source dataset
uspto-grants-1999_10
Patent number
US05972978

Reaction notes

Loading…