Water → Methyl 2-hydroxy-4-(3-trimethylsilanyl-propyloxy)-benzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl gentisate (16.8 g, 0.1 mole) and potassium carbonate (15.2 g, 0.11 mole) in 80 ml of DMF in a nitrogen atmosphere at 80° C. is added chloropropyl trimethyl silane (16.6 g, 0.11 mole) drop by drop over a 20-minute period. The mixture is heated to 90° C. for 8 hours. It is cooled and then poured into 200 ml of water. Extraction is performed with diisopropyl ether. The organic phase is washed with water, dried with sodium sulfate, and then concentrated. After silica chromatography of the resulting yellow oil (eluent: Heptane/CH2Cl2 90:10) we obtain 3.3 g of a clean fraction of methyl 2-hydroxy-4-(3-trimethylsilanyl-propyloxy)-benzoate.

Provenance & Evidence