2-amino-6-ethylphenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Ethyl-2-aminophenol (0.88 g, 6.4 mmol), 2-chloroacetyl chloride (0.80 g, 7.0 mmol) and K2CO3 (1.86 g, 13.5 mmol) were mixed according to GP1. Purified by column chromatography (SiO2; CH2Cl2/MeOH 99:1) to give the title compound (0.69 g, 61%). Rf=0.54 (heptanes/EtOAc 1:1); 1H NMR (CDCI3) d 9.29 (s, 1H), 6.92-6.85 (m, 2H), 6.71 (dd, J=7.0 Hz, J=2.6 Hz), 4.62 (s, 2H), 2.65 (q, J=7.6 Hz, 2H), 1.20 (t, J=7.6 Hz, 3H); 13C NMR (CDCl3) d 166.8, 141.6, 133.0, 126.1, 124.4, 122.5, 114.0, 67.3, 22.9, 14.4. Purified by column chromatography (SiO2; CH2Cl2/MeOH 99:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Ethyl-2-aminophenol (0.88 g, 6.4 mmol), 2-chloroacetyl chloride (0.80 g, 7.0 mmol) and K2CO3 (1.86 g, 13.5 mmol) were mixed according to GP1. Purified by column chromatography (SiO2; CH2Cl2/MeOH 99:1) to give the title compound (0.69 g, 61%). Rf=0.54 (heptanes/EtOAc 1:1); 1H NMR (CDCl3) δ 9.29 (s, 1H), 6.92-6.85 (m, 2H), 6.71 (dd, J=7.0 Hz, J=2.6 Hz), 4.62 (s, 2H), 2.65 (q, J=7.6 Hz, 2H), 1.20 (t, J=7.6 Hz, 3H); 13C NMR (CDCl3) δ 166.8, 141.6, 133.0, 126.1, 124.4, 122.5, 114.0, 67.3, 22.9, 14.4. Purified by column chromatography (SiO2; CH2Cl2/MeOH 99:1)