1-(2-Methoxy-4-nitrophenoxy)-2-methylpropan-2-ol → 1-(4-Amino-2-methoxyphenoxy)-2-methylpropan-2-ol

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Reaction Steps

A stirred EtOH suspension (320 mL) containing 1-(2-methoxy-4-nitrophenoxy)-2-methylpropan-2-ol Part A (13.6 g, 56.4 mmol) and 10% Pd/C (0.25 g) was hydrogenated under 60 psi H2 for 6 hr. HPLC analysis revealed no starting nitro catechol ether remained. The resultant black suspension was filtered through a fiberglass filter paper under a blanket of N2 gas. The resultant clear wine colored solution was immediately concentrated using a rotary evaporator under vacuum to yield 12.4 of desired product as a dark orange oil which was used without further purification. 1H NMR (CDCl3) δ 1.29 (s, 6H), 3.40, (br s, 2H), 3.74 (s, 2H), 3.78 (s, 3H), 6.20 (dd, J=8.35 Hz, 2.64 Hz, 1H), 6.28 (d, J=2.64 Hz, 1H), 6.76 (d, J=8.35 Hz, 1H); 13C NMR (CDCl3) δ 25.90, 55.67, 70.02, 80.30, 100.76, 106.81, 118.27, 141.55, 141.93, 150.99; HPLC (Method #1): 0.88 min retention time; LCMS (ES): m/z 212.1 [M+H].

Provenance & Evidence