Methyl Salicylate → Methyl 2-(1-methoxycarbonylpentoxy)benzoate

Reaktionsgleichung

[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH2:24][CH2:25][CH2:26][CH3:27])[C:20]([O:22][CH3:23])=[O:21]>C(#N)C>[CH3:23][O:22][C:20]([CH:19]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])[CH2:24][CH2:25][CH2:26][CH3:27])=[O:21]

Komponenten

Versuchsvorschrift

15.2 g of methyl salicylate and 18.0 g of potassium carbonate were introduced into 125 ml of acetonitrile in a 250 ml flask under an argon atmosphere and, at room temperature, 20.9 g of methyl 2-bromohexanoate were added. The colourless suspension was heated under reflux with stirring for 16 hours, and the progress of the reaction was checked by thin-layer chromatography. After cooling to room temperature, the suspension was filtered and the residue was washed with acetone. Concentration of the filtrate in vacuo resulted in 27.8 g (99% of theory) of methyl 2-(1-methoxycarbonylpentoxy)benzoate as yellow oil.