4-Hydroxybenzaldehyde → 4-{((2-Methyl-2-sulfanylpropyl)amino)methyl}phenol

Participants

Reaction Steps

To a hot solution of 4-hydroxybenzaldehyde (8.90 g, 72.8 mmol) in CHCl3 (250 mL) were added 1-amino-2-methyl-2-propanethiol hydrochloride (10.32 g, 72.8 mmol), K2CO3 (20.2 g, 146 mmol), and MgSO4 (5 g). The mixture was stirred and refluxed under nitrogen atmosphere for 3 hours. After cooling, the mixture was filtered to remove inorganic solid, and the filter cake was washed through with MeOH (2×100 mL). Evaporation of the filtrate afforded the product 5a as a white solid (15 g, 98%). mp 85-87° C.; 1H NMR (CDCl3, 300 MHz) δ 7.38 (d, J=8.5 Hz, 2H), 6.76 (d, J=8.5 Hz, 2H), 5.74 (s, 1H), 3.25 (d, J=12.1 Hz, 1H), 3.01 (d, J=12.1 Hz, 1H), 1.59 (s, 3H), 1.58 (s, 3H).

Provenance & Evidence