Benzenesulfinic acid, sodium salt → 6-hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone
Reaction equation
Cl[CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14].[C:15]1([S:21]([O-:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Na+]>C(#N)C>[OH:13][C:12]1[C:3]([CH2:2][S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][CH2:5]2Participants
4
Procedure
A mixture of 5-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone (10.0 g, 48 mmol), sodium phenylsulfinate (23.4 g, 142 mmol) and acetonitrile (100 mL) was stirred at reflux under nitrogen overnight. The mixture was poured onto ice. The precipitate was isolated by filtration, air dried, and crystallized from methanol-dichloromethane-ethyl acetate to give 6-hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone as a cream solid, 12.16 g, 84% yield. NMR spectrum was consistent with structure.