Benzoic acid derivatives are important molecular systems in the pharmaceutical industry. Salicylic acid is distinct among the derivatives of benzoic acid due to the presence of an intramolecular hydrogen bond. With a view to study the evolution of inter and intramolecular hydrogen bonding at shorter length scales, in situ high pressure Raman spectroscopic measurements, angle dispersive X-ray diffraction experiments, and density functional theory (DFT) based first principle calculations have been carried out on crystalline salicylic acid. Subtle structural modifications are noted across similar to 1 GPa leading to structural phase transition to a new crystalline phase above 7 GPa which is reversible. Substantial softening of the OH stretching Raman mode associated with intramolecular hydrogen bond is observed prior to the transition pressure. Possible molecular configurations associated with tautomerization are discussed with the aid of DFT calculations.