Synthesis
Method D: Catechol (1 eq.) was added to a suspension of K2CO3 (1 eq.) in acetone (20 mL) and the mixture was stirred at room temperature for 2 hours. Then 1-iodopropane (1.2 eq.) was added and the reaction mixture was heated to reflux and the reaction progress was monitored by TLC (CHCl3). After completion of the reaction, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with benzene (30 mL) and washed with 10% aqueous NaOH (40 mL). The organic layer was dried with anhydrous Na2SO4 and concentrated under reduced pressure to give o-propoxyphenol. The basic aqueous layer was cooled in an ice bath and acidified with concentrated HCl. Solid o-propoxyphenol was collected from the mixture by vacuum filtration. The yield of o-propoxyphenol was 51% and its structure was confirmed by GC, 1H NMR, 13C NMR, MS and IR.
