Thionyl Chloride → 4-Methylnaphthalene-1-carbonyl chloride

HRID 574598Notes

Reaction equation

HRID 574598 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>ClCCl>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([Cl:17])=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 30142854-Methyl-1-naphthalenecarboxylic acid

Product 1

HCID 248874124-Methylnaphthalene-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.35 g (1.89 mmol) of 4-methyl-1-napthoic acid in 3 mL of dry dichloromethane under argon, was added 2.5 ml (34.3 mmol) of thionyl chloride. The solution was refluxed for 4 hrs and the solvent and excess thionyl chloride were removed by vacuum distillation to give a red oil, which was used without further purification.

Workup

  1. temperatureThe solution was refluxed for 4 hrs
  2. customthe solvent and excess thionyl chloride were removed by vacuum distillation
  3. customto give a red oil, which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-e7bf472ec26c4ba8bd4fa69a29f493ff
Source dataset
uspto-grants-2015_05
Patent number
US09034895B2

Reaction notes

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