boron trifluoride diethyl etherate in dichloromethane 1.) 0 deg C, 0.5 h, 2.) 25 deg C, 1.5 h;

1: 83 percent / chromium trioxide, pyridine / CH2Cl2 / 0.17 h / 25 °C 2: 94 percent / 1.) boron trifluoride etherate / CH2Cl2 / 1.) 0 deg C, 0.5 h, 2.) 25 deg C, 1.5 h View Scheme

1: 97.5 percent / lithium aluminum hydride / diethyl ether / 1.) 0 deg C, 0.5 h, 2.) 25 deg C, 5 h 2: 83 percent / chromium trioxide, pyridine / CH2Cl2 / 0.17 h / 25 °C 3: 94 percent / 1.) boron trifluoride etherate / CH2Cl2 / 1.) 0 deg C, 0.5 h, 2.) 25 deg C, 1.5 h View Scheme

1: 1.) aluminium chloride, 2.) sodium dithionite, sodium hydroxide / 1.) 1,1,2,2-tetrachloroethane, room temperature, 16 h; steam-bath, 2 h, 2.) methanol, room temperature, 21 h, reflux, 24 h 2: 88 percent / hydrogen / palladium-carbon / acetic acid / 1.5 h / Ambient temperature 3: 59 percent / lithium aluminium hydride / diethyl ether 4: 62 percent / pyridine 5: 80 percent / lithium bromide / acetone / 24 h / Ambient temperature 6: magnesium (from magnesium chloride and potassium metal, 3-(4-methoxyphenyl)propanal / tetrahydrofuran 7: 74 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h 8: 54 percent / hydrogen chloride / CH2Cl2 / 0.5 h / -25 °C View Scheme

1: 88 percent / hydrogen / palladium-carbon / acetic acid / 1.5 h / Ambient temperature 2: 59 percent / lithium aluminium hydride / diethyl ether 3: 62 percent / pyridine 4: 80 percent / lithium bromide / acetone / 24 h / Ambient temperature 5: magnesium (from magnesium chloride and potassium metal, 3-(4-methoxyphenyl)propanal / tetrahydrofuran 6: 74 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h 7: 54 percent / hydrogen chloride / CH2Cl2 / 0.5 h / -25 °C View Scheme

1: 59 percent / lithium aluminium hydride / diethyl ether 2: 62 percent / pyridine 3: 80 percent / lithium bromide / acetone / 24 h / Ambient temperature 4: magnesium (from magnesium chloride and potassium metal, 3-(4-methoxyphenyl)propanal / tetrahydrofuran 5: 74 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h 6: 54 percent / hydrogen chloride / CH2Cl2 / 0.5 h / -25 °C View Scheme

1: 62 percent / pyridine 2: 80 percent / lithium bromide / acetone / 24 h / Ambient temperature 3: magnesium (from magnesium chloride and potassium metal, 3-(4-methoxyphenyl)propanal / tetrahydrofuran 4: 74 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h 5: 54 percent / hydrogen chloride / CH2Cl2 / 0.5 h / -25 °C View Scheme

1: magnesium (from magnesium chloride and potassium metal, 3-(4-methoxyphenyl)propanal / tetrahydrofuran 2: 74 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h 3: 54 percent / hydrogen chloride / CH2Cl2 / 0.5 h / -25 °C View Scheme

1: 80 percent / lithium bromide / acetone / 24 h / Ambient temperature 2: magnesium (from magnesium chloride and potassium metal, 3-(4-methoxyphenyl)propanal / tetrahydrofuran 3: 74 percent / pyridinium chlorochromate / CH2Cl2 / 4.5 h 4: 54 percent / hydrogen chloride / CH2Cl2 / 0.5 h / -25 °C View Scheme