Acetone → HCID 10970592, compound

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[C:9]([Br:21])[CH:10]=[CH:11][C:12]=2[O:17][CH:18]([CH3:20])[CH3:19])[CH:7]=1)=[O:5])[CH3:2].[CH3:22]C(C)=O.COS(OC)(=O)=O>N>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH3:22])[C:13]2[C:8](=[C:9]([Br:21])[CH:10]=[CH:11][C:12]=2[O:17][CH:18]([CH3:20])[CH3:19])[CH:7]=1)=[O:5])[CH3:2]

Participants

Procedure

To a solution of 4.92 g (13.9 mmol) ethyl-8-bromo-4-hydroxy-5-isopropoxy-2-naphthoate in 150 mL acetone 4.80 g (34.8 mmol) K2CO3 and dropwise 4.90 g (38.7 mmol) dimethylsulfate at room temperature were added. Subsequently the reaction mixture was refluxed for 10 h and after that 60 mL of concentrated ammonia was added. Solvent was removed under vacuum and the residue was partitioned between water and dichloromethane. The combined organic phases were washed three times with 2N NaOH solution and two times with water. The organic phase was dried (MgSO4) and concentrated under vacuum. The residue was recrystallized from diethylether to give 5.00 g (99%) ethyl-8-bromo-5-isopropoxy-4-methoxy-2-naphthoate as colorless needles (m.p. 62° C.).