1: 1.) O3, 2.) (CH3)2S / 1.) MeOH, -60 deg C, 3.5 h, 2.) MeOH, 30 deg C, 10 min 2: 95 percent / 85percent H3PO4 / 0.08 h / 50 °C 3: 94 percent / 85percent KOH / ethanol / 2 h / Heating View Scheme

1: 1.) O3, 2.) (CH3)2S / 1.) MeOH, -60 deg C, 3.5 h, 2.) MeOH, 30 deg C, 10 min 2: 95 percent / 85percent H3PO4 / 0.08 h / 50 °C View Scheme

hydrogen; palladium on activated charcoal in methanol

palladium in methanol

hydrogen bromide; acetic acid Erwaermen des Reaktionsprodukts mit wss. Natronlauge;

1: 87 percent / K2CO3 / acetone / Heating 2: 94 percent / 2,6-di-tert-butyl-4-methylphenol (BHT) / various solvent(s) / Heating 3: 97 percent / Et3N, DMAP / CH2Cl2 4: 90 percent / H2 / 5percent Rh/C / ethanol 5: 92 percent / LiAlH4 / tetrahydrofuran / 0 - 20 °C 6: 82 percent / Ph3P, DEAD / tetrahydrofuran / 0 °C 7: 93 percent / n-Bu4NF / tetrahydrofuran 8: K2CO3 / acetone / Heating 9: 1 N aq. NaOH / methanol View Scheme

2,6-di-tert-butyl-4-methyl-phenol in various solvent(s) Heating;

2,6-di-tert-butyl-4-methyl-phenol; nitrogen

1: K2CO3 / acetone / 16 h / 0 - 20 °C 2: BCl3 / chlorobenzene / 8 h / 20 °C View Scheme

1: 1.) O3, 2.) (CH3)2S / 1.) MeOH, -60 deg C, 3.5 h, 2.) MeOH, 30 deg C, 10 min 2: 95 percent / 85percent H3PO4 / 0.08 h / 50 °C 3: 94 percent / 85percent KOH / ethanol / 2 h / Heating 4: SOCl2, DMF / Ambient temperature View Scheme