Ethanol → Ethyl 10-chloroanthracene-1-carboxylate
Reaction equation
[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]([OH:18])=[O:17].OS(O)(=O)=O.[CH3:24][CH2:25]O>>[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]([O:18][CH2:24][CH3:25])=[O:17]Participants
4
Procedure
10-Chloroanthracene-1-carboxylic acid (37A, 17.3 g, 0.0674 mol), conc. H2SO4 (1.0 mL), and abs. EtOH (500 mL) was refluxed for 3 days using 4Å molecular sieves in a Soxhlet extractor to remove H2O. The solvent was removed and then partitioned between EtOAc and satd. NaHCO3. The solvent was then removed from the organic layer to give 14.86 g (77%) of ethyl 10-chloroanthracene-1-carboxylate, which was used without further purification.