Thionyl Chloride → 6-(Chlorocarbonyl)naphthalen-2-yl acetate

HRID 1581450Notes

Reaction equation

HRID 1581450 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([OH:17])=O)[CH:9]=[CH:8]2)(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([Cl:20])=[O:17])[CH:9]=[CH:8]2)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 870386-(Acetyloxy)-2-naphthalenecarboxylic acid

Product 1

HCID 157248096-(Chlorocarbonyl)naphthalen-2-yl acetateYield 101.8%

Conditions

Temperature
79 °C

Procedure

30 Grams (130.3 mmol) of 6-acetoxy-2-naphthoic acid and 155 g (260 mmol) of purified thionyl chloride were placed in a reactor, and the mixture was refluxed under heat (79° C.) for 4 hours. Thionyl chloride was distilled off under atmospheric pressure, 150 ml of toluene was added, and toluene and thionyl chloride were distilled off under reduced pressure, to give 33 g of an end compound (yield 98%).

Workup

  1. temperaturethe mixture was refluxed
  2. distillationThionyl chloride was distilled off under atmospheric pressure, 150 ml of toluene
  3. additionwas added
  4. distillationtoluene and thionyl chloride were distilled off under reduced pressure

Sources & evidence

ORD record
ord-4f4575ee9c0d438a9df4d5b280244db8
Source dataset
uspto-grants-2004_05
Patent number
US06730371B2

Reaction notes

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