Thionyl Chloride → 4-Acetyl-1-naphthalenecarbonyl chloride

HRID 576041Notes

Reaction equation

HRID 576041 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]([OH:20])=O)=[CH:10][CH:9]=1)(=[O:7])[CH3:6]>C1(C)C=CC=CC=1>[C:5]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]([Cl:3])=[O:20])=[CH:10][CH:9]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 668663434-Acetylnaphthalene-1-carboxylic acid

Product 1

HCID 866498014-Acetyl-1-naphthalenecarbonyl chlorideYield 98.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Thionyl chloride (35.00 g, 0.29 mol) was added to a solution of 4-acetyl-1-naphthalenecarboxylic acid (51.70 g, 0.24 mol) in toluene (350 mL). The mixture was warmed to 90° C. for 8.5 h. After cooling to 25° C., the solvent was removed under reduced pressure to give the title product as an off-white solid (55.1 g, 98.7% yield).

Workup

  1. temperatureAfter cooling to 25° C.
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7ecbf2ef910943bfa57b2f5b2e0d40d7
Source dataset
uspto-grants-2015_05
Patent number
US09035101B2

Reaction notes

Loading…