2-Naphthoic acid → 2-Naphthoyl chloride

HRID 1421922Notes

Reaction equation

HRID 1421922 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-3a727f4dd8f94182ae4ead14ebb3134c
Source dataset
uspto-grants-2000_06
Patent number
US06080770

Reaction notes

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