Hydrogen Bromide → 4-(4-Hydroxyphenyl)butanoic acid

Participants

Reaction Steps

4-(4-Methoxyphenyl)butanoic acid (0.97 g, 5 mmol) was mixed with HBr (50 mL) and acetic acid galacial (80 mL). The mixture was refluxed for 12 h (monitored by TLC), poured into ice, stirred for 1 h, and then extracted with DCM. The solvent was evaporated in vacuo to give the title compound (0.83 g, 92%). NMR (400 MHz in CDCl3, Bruker AVANCE-400): δ 1.72 (m, 2H, CH2), 2.16 (t, 2H, CH2, J=7.4 Hz), 2.45 (t, 2H, CH2, J=7.6 Hz), 6.65 (d, 2H, Ar—H, J=8.3 Hz), 6.95 (d, 2H, Ar—H, J=8.3 Hz).

Provenance & Evidence