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]=1Participants
3
Procedure
The 2-methyl-3,5-dihydro-5,9b-o-benzenobenz[e]isoindol-1-(2H)-one starting material was prepared as follows: a mixture of 25 g of 9-anthroic acid and 75 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 28.3 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