Potassium Carbonate → HCID 53641489, compound

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5](OC)=O)[C:3]=1[OH:12].[C:13]([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CC(C)=O>[CH3:13][O:12][C:3]1[C:4](=[CH:9][CH:10]=[CH:11][C:2]=1[Cl:1])[CH:5]=[CH:20][C:21]([O:23][CH3:24])=[O:22]

Participants

Procedure

A mixture of 3-chlorosalicylic acid (20.2 g, 0.117 mol), Na2SO4 (5.0 g, 0.035 mol), MeOH (100 mL), and saturated methanolic HCl (40 mL) was heated under reflux for 2 days. The mixture was filtered, concentrated, and partitioned between ether and H2O. The organic phase was washed with saturated aqueous NaHCO3, dried (MgSO4) and concentrated to give a yellow oil (17.4 g). A mixture of methyl 3-chlorosalicylate (17.4 g, 0.093 mol), K2CO3 (12.9 g, 0.093 mol), and acetone (100 mL) was heated for 10 minutes. Additional acetone (100 mL) and methyl bromoacetate (14.3 g, 0.093 mol) were added and heating was continued for 18 hours. The mixture was cooled, concentrated, and partitioned between ether and H2O. The organic phase was dried (MgSO4) and concentrated to give a pale yellow oil (24.6 g, 80%).