\(\mathrm{SOCl_2}\) converts alcoholic (including benzylic) \(\mathrm{-OH}\) groups into \(\mathrm{-Cl}\), but the phenolic \(\mathrm{-OH}\) is not replaced because its C-O bond has partial double bond character.
The substrate has three hydroxyl groups: a phenolic \(\mathrm{-OH}\) on the benzene ring, a secondary benzylic alcohol \(\mathrm{-OH}\) on the saturated ring, and a primary benzylic alcohol \(\mathrm{-CH_2OH}\). \(\mathrm{SOCl_2}\) reacts with alcohols: \(\mathrm{R-OH + SOCl_2 \to R-Cl + SO_2 + HCl}\). The secondary alcoholic \(\mathrm{-OH}\) becomes \(\mathrm{-Cl}\), and \(\mathrm{-CH_2OH}\) becomes \(\mathrm{-CH_2Cl}\). The phenolic C-O bond has partial double bond character (the oxygen lone pair is delocalised into the ring), so it is not cleaved and the phenolic \(\mathrm{-OH}\) stays. Product: phenolic \(\mathrm{-OH}\) retained, ring \(\mathrm{CH-Cl}\) and \(\mathrm{-CH_2Cl}\). This is option (3). Answer: (3) (structure with phenolic OH, ring CHCl and CH2Cl)
