Why is methyl salicylate not appreciably soluble in waterSol

Why is methyl salicylate not appreciably soluble in water?

Solution

Methyl salicylate is not soluble in water due to the presence of benzene ring which is hydrophobic in nature leading to dispersion forces between the ester molecules. Secondly, the presence of OH group gives rise to hydrogen bonding with the water molecules. This hydrogen bonding is weak in nature since the dispersion forces between the two benzene rings are more leading to decreased solubility of methyl salicylate in water.