Resorcinol → 3-(propan-2-yloxy)phenol

Participants

Reaction Steps

To a mixture of 3-hydroxyphenol (20.0 g, 0.182 mmoL), 2-iodopropane (30.9 g, 0.182 mmoL) in ethanol (25 mL) at refluxing was added KOH (88%, 12.2 g, 0.191 mmoL) in water (30 mL) over a period of 60 min. The resulting mixture was refluxed for 3 hours. The mixture was poured into 1N NaOH and extracted with ether (1×). The aqueous layer was acidified with 10% HCl to pH 5 and extracted with ether (2×). The combined extracts were washed with brine (1×), dried over MgSO4 and concentrated. The residue was purified on silica gel eluting with ethyl acetate:hexane (1:8) to give the desired product as a colorless liquid (11.7 g, 43%). This was used directly in the next step. 1H NMR (500 MHz, CDCl3) δ ppm 7.10 (t, 1H) 6.47 (d, J=7.32 Hz, 1H) 6.36-6.42 (m, 1H) 4.70 (s, 1H) 4.45-4.55 (m, 1H) 4.13 (q, J=7.32 Hz, 1H) 1.32 (d, 6H). MS m/z (DCI) 153.0 (M+H)+.

Provenance & Evidence