potassium hydroxide in methanol; water 12 h; Ambient temperature;

1: 2) boron trifluoride etherate / 1) dirhodium tetraacetate / 1) CH2Cl2, 25 h, 2) RT, 1 h 2: NaBH4, CeCl3*7H2O / CH2Cl2; ethanol / 0.17 h 3: 70 percent / para-methylated variant of Martin reagent / CH2Cl2 / 1) -100 deg C, 6 h, 2) warm to RT, 3) RT, 12 h 4: 86 percent / KOH / methanol; H2O / 12 h / Ambient temperature View Scheme

1: 62 percent / hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 1) 120 deg C, 0.5 h, 2) 185 deg C, 1.5. h 2: 2) boron trifluoride etherate / 1) dirhodium tetraacetate / 1) CH2Cl2, 25 h, 2) RT, 1 h 3: NaBH4, CeCl3*7H2O / CH2Cl2; ethanol / 0.17 h 4: 70 percent / para-methylated variant of Martin reagent / CH2Cl2 / 1) -100 deg C, 6 h, 2) warm to RT, 3) RT, 12 h 5: 86 percent / KOH / methanol; H2O / 12 h / Ambient temperature View Scheme

1: 90 percent / trimethylsilyl chloride, NaI / acetonitrile / 1 h 2: 62 percent / hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 1) 120 deg C, 0.5 h, 2) 185 deg C, 1.5. h 3: 2) boron trifluoride etherate / 1) dirhodium tetraacetate / 1) CH2Cl2, 25 h, 2) RT, 1 h 4: NaBH4, CeCl3*7H2O / CH2Cl2; ethanol / 0.17 h 5: 70 percent / para-methylated variant of Martin reagent / CH2Cl2 / 1) -100 deg C, 6 h, 2) warm to RT, 3) RT, 12 h 6: 86 percent / KOH / methanol; H2O / 12 h / Ambient temperature View Scheme

1: NaBH4, CeCl3*7H2O / CH2Cl2; ethanol / 0.17 h 2: 70 percent / para-methylated variant of Martin reagent / CH2Cl2 / 1) -100 deg C, 6 h, 2) warm to RT, 3) RT, 12 h 3: 86 percent / KOH / methanol; H2O / 12 h / Ambient temperature View Scheme

1: 70 percent / para-methylated variant of Martin reagent / CH2Cl2 / 1) -100 deg C, 6 h, 2) warm to RT, 3) RT, 12 h 2: 86 percent / KOH / methanol; H2O / 12 h / Ambient temperature View Scheme

1: acetone; chromium (VI)-oxide; aqueous sulfuric acid 2: petroleum ether; manganese (II)-acetate; oxygen 3: copper (I)-chloride; ammonium chloride; aqueous acetone / Reagens 4: Sauerstoff 4: aqueous KOH-solution View Scheme

1: lithium alanate; diethyl ether 2: acetone; chromium (VI)-oxide; aqueous sulfuric acid 3: petroleum ether; manganese (II)-acetate; oxygen 4: copper (I)-chloride; ammonium chloride; aqueous acetone / Reagens 4: Sauerstoff 5: aqueous KOH-solution View Scheme

1: lithium alanate; diethyl ether 2: acetone; chromium (VI)-oxide; aqueous sulfuric acid 3: petroleum ether; manganese (II)-acetate; oxygen 4: copper (I)-chloride; ammonium chloride; aqueous acetone / Reagens 4: Sauerstoff 5: aqueous KOH-solution View Scheme

potassium hydroxide