Hydrochloric Acid → 4-((4-(Hydroxymethyl)phenyl)diazenyl)-3-methoxyphenol

Participants

Reaction Conditions

Reaction Steps

4-Aminobenzyl alcohol (0.275 g, 2.24 mmol) and NaNO2 (0.16 g, 2.35 mmol) were dissolved in 7.5 mL EtOH:water (1.5:1) and added to 2 N HCl solution (4.5 mL) and reaction mixture stirred at 0° C. for 1 hour. 3-methoxyphenol (0.25 g, 2.01 mmol) in EtOH was added, followed by addition of NaOAc (0.15 g) at 0° C. and remaining procedure followed as described for compound 1 to obtain compound 2. Yield: 0.435 g (84%). 1H NMR (500 MHz, CD3SOCD3) δ 3.34 (bs, 4H, OMe, —OH), 4.55 (bs, 2H, Hf), 5.31 (s, 1H, phenol-OH), 6.43-6.46 (m, 1H, Hb), 6.57-6.60 (m, 1H, He), 7.44-7.48 (m, 2H, He), 7.53-7.57 (m, 1H, Ha), 7.69-7.74 (m, 2H, Hd). 13C NMR (125 MHz, CD3SOCD3) δ 55.7 (OMe), 62.5 (Cf), 99.9 (Cc), 107.9 (Cb), 117.4 (Ci), 121.9 (Cd), 127.0 (Ce), 134.8 (Ca), 144.7 (Ck), 151.5 (Cj), 158.9 (Ch), 162.6 (Cg). ESI-MS: [M+H]+ C14H15N2O3 calcd 259.1083, obsd 259.10.

Provenance & Evidence