lithium aluminium tetrahydride in diethyl ether 2 h; Heating;

potassium carbonate in acetone 18 h; Heating;

chromium(VI) oxide; sulfuric acid in water; acetone T=20°C; Jones oxidation; 0.0833333 h;

sodium acetate; pyridinium chlorochromate in dichloromethane 3 h;

sodium tetrahydroborate in N,N-dimethyl-formamide T=0°C; 4 h; Yield givenYields of byproduct given;

1: 89 percent / conc. H2SO4 / 18 h / Heating 2: 1.) AlCl3, HCl / 1.) 0 deg C, 6 h, ether; 2.) 70 deg C, 1 h, water 3: 81 percent / K2CO3 / acetone / 1.5 h / Heating 4: 1.) NaBH4; 2.) 2N NaOH 3.) 2N HCl / 1.) MeOH, 25 deg C, 0.5 h; 2.) 60 deg C, 0.25 h 5: 73 percent / K2CO3 / acetone / 18 h / Heating View Scheme

1: 81 percent / K2CO3 / acetone / 1.5 h / Heating 2: 1.) NaBH4; 2.) 2N NaOH 3.) 2N HCl / 1.) MeOH, 25 deg C, 0.5 h; 2.) 60 deg C, 0.25 h 3: 73 percent / K2CO3 / acetone / 18 h / Heating View Scheme

1: 40 percent / 1.) KOH, NaOH, water 2.) conc. HCl / 1.) 140 deg C, 0.5 h; 250 deg C, 1.5 h; 265 deg C, 0.75 h; allowed to cool to 200 deg C 2: 89 percent / conc. H2SO4 / 18 h / Heating 3: 1.) AlCl3, HCl / 1.) 0 deg C, 6 h, ether; 2.) 70 deg C, 1 h, water 4: 81 percent / K2CO3 / acetone / 1.5 h / Heating 5: 1.) NaBH4; 2.) 2N NaOH 3.) 2N HCl / 1.) MeOH, 25 deg C, 0.5 h; 2.) 60 deg C, 0.25 h 6: 73 percent / K2CO3 / acetone / 18 h / Heating View Scheme

1: 1.) NaBH4; 2.) 2N NaOH 3.) 2N HCl / 1.) MeOH, 25 deg C, 0.5 h; 2.) 60 deg C, 0.25 h 2: 73 percent / K2CO3 / acetone / 18 h / Heating View Scheme

1: fuming H2SO4 / 8 h / 170 °C 2: 40 percent / 1.) KOH, NaOH, water 2.) conc. HCl / 1.) 140 deg C, 0.5 h; 250 deg C, 1.5 h; 265 deg C, 0.75 h; allowed to cool to 200 deg C 3: 89 percent / conc. H2SO4 / 18 h / Heating 4: 1.) AlCl3, HCl / 1.) 0 deg C, 6 h, ether; 2.) 70 deg C, 1 h, water 5: 81 percent / K2CO3 / acetone / 1.5 h / Heating 6: 1.) NaBH4; 2.) 2N NaOH 3.) 2N HCl / 1.) MeOH, 25 deg C, 0.5 h; 2.) 60 deg C, 0.25 h 7: 73 percent / K2CO3 / acetone / 18 h / Heating View Scheme