Methanol → Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate
Reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O.[CH3:19]O>>[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([O:14][CH3:19])=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1Participants
4
Procedure
To a solution of 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (16 g, 0.084 mol) in MeOH was added thionylchloride (23 g, 0.2 mol). The mixture was then stirred at rt for 12 h. The solvent was removed under vacuum and the residue was taken up in EtOAc (200 ml). The organic layer was washed with a 10% aqueous solution of NaHCO3, dried over MgSO4 and evaporated to give 16 g (94%) of the titled compound as a liquid. TLC: Chloroform/MeOH (9/1), Rf=0.9.