9-Anthracenecarboxylic acid → Anthracene-9-carbonyl chloride

Reaction equation

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

Participants

Reactant 2

HCID 22019-Anthracenecarboxylic acid

HCID 24386Thionyl Chloride

Product 1

HCID 167528Anthracene-9-carbonyl chloride

Procedure

A mixture of 18.85 g of 9-anthroic acid and 60 ml of thionyl chloride is heated under reflux for 1 hour. The excess thionyl chloride is removed under vacuum (30 mm; 90° bath temperature); 50 ml of toluene is added and the mixture is concentrated again. This operation is repeated once more to give 20.6 g of 9-anthroyl chloride as a very moisture-sensitive, yellow solid.

Workup

temperatureis heated
temperatureunder reflux for 1 hour
customThe excess thionyl chloride is removed under vacuum (30 mm; 90° bath temperature)
addition50 ml of toluene is added
concentrationthe mixture is concentrated again

Sources & evidence

ORD record: ord-3ed3d34efb9e4ae59d549b4175592822
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04077977

Reaction notes

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