Methanol → HCID 12133075, compound

Participants

Reaction Conditions

Reaction Steps

Carbon tetrachloride (28 mL) was added dropwise to a mixture of 2,6-diisopropylphenol (37.5 mL), copper powder (2 g), methanol (150 mL), and 40% aqueous solution of sodium hydroxide (150 mL), at 40–50° C. The reaction temperature was warmed to about 60° C., and the resulting mixture was allowed to stir for 4 hours. The mixture was poured into water and extracted with toluene (3×). The combined organics were washed (brine), dried over sodium sulfate and concentrated. Chromatography with ethyl ether:hexanes as the eluent (gradient 5/95 to 8/92) provided material that precipitated as a white solid upon addition of hexane. The white solid was collected by filtration to provide the title compound (1.06 g); 1H-NMR(CDCl3) δ=1.29 (d, 12H, CH(CH3)2), 3.16 (m, 2H, CH (CH3)2), 3.87 (S, 3H, OCH3), 5.22 (S, 1H, OH), 7.78 (S, 2H, ArH).

Provenance & Evidence