2,6-di-tert-butyl-4-methyl-phenol in m-xylene T=140°C; 15 h;

1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C View Scheme

2,6-di-tert-butyl-4-methyl-phenol in m-xylene Heating;

1: 88 percent / HNO3 / acetic acid / 0.75 h / 0 °C 2: 90 percent / NaBH4 / methanol / 24 h / Ambient temperature 3: 83 percent / TsOH / toluene / 10 h / Heating 4: 95 percent / 5N aq. HCl / ethanol / 6 h / Heating 5: 1.) aq. H2SO, NaNO2, 2.) aq. KI / 1.) 0 deg C, 1 h, 2.) RT, overnight View Scheme

1: 95 percent / 5N aq. HCl / ethanol / 6 h / Heating 2: 1.) aq. H2SO, NaNO2, 2.) aq. KI / 1.) 0 deg C, 1 h, 2.) RT, overnight View Scheme

1: 90 percent / NaBH4 / methanol / 24 h / Ambient temperature 2: 83 percent / TsOH / toluene / 10 h / Heating 3: 95 percent / 5N aq. HCl / ethanol / 6 h / Heating 4: 1.) aq. H2SO, NaNO2, 2.) aq. KI / 1.) 0 deg C, 1 h, 2.) RT, overnight View Scheme