1: BF3-Et2O / 5 °C 2: 66 percent / (i-Pr)2NEt / CH2Cl2 3: 91 percent / 1M NaOH / methanol 4: 95 percent / MnO2 / CH2Cl2 5: 94 percent / NaOH / ethanol 6: 96 percent / 30percent H2O2, 5percent NaOH / methanol 7: 19 percent / conc. HCl / methanol / 70 °C View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: 92 percent / 30percent H₂O₂, 5percent NaOH / methanol; dioxane<br />2: 1.) BF₃*Et₂O, 2.) NaBH₄ / 1.) benzene, 0 deg C, 2.) THF<br />3: 66 percent / H₂ / 10percent Pd-C / methanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1.) BF₃*Et₂O, 2.) NaBH₄ / 1.) benzene, 0 deg C, 2.) THF<br />2: 66 percent / H₂ / 10percent Pd-C / methanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 91 percent / ammonium chloride / methanol / 4 h / Heating<br />2: 94 percent / 1.) n-butyl lithium / hexane; diethyl ether / 1.) -78 deg C, 10 min, 2.) -78 deg C to room temperature, 3 h<br />3: 93 percent / potassium hydroxide / ethanol / 4 h<br />4: 87 percent / conc. HCl / dioxane; methanol / 1.5 h / Ambient temperature<br />5: 92 percent / 30percent H₂O₂, 5percent NaOH / dioxane; methanol / 3 h / Ambient temperature<br />6: 1.) boron trifluoride etherate, 2.) sodium borohydride / 1.) benzene, 20 min, 2.) THF, room temperature, 2 h<br />7: 66 percent / hydrogen / 10percent Pd/C / methanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 93 percent / potassium hydroxide / ethanol / 4 h<br />2: 87 percent / conc. HCl / dioxane; methanol / 1.5 h / Ambient temperature<br />3: 92 percent / 30percent H₂O₂, 5percent NaOH / dioxane; methanol / 3 h / Ambient temperature<br />4: 1.) boron trifluoride etherate, 2.) sodium borohydride / 1.) benzene, 20 min, 2.) THF, room temperature, 2 h<br />5: 66 percent / hydrogen / 10percent Pd/C / methanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: 86 percent / potassium carbonate / dimethylformamide / 3 h / Heating<br />2: 91 percent / ammonium chloride / methanol / 4 h / Heating<br />3: 94 percent / 1.) n-butyl lithium / hexane; diethyl ether / 1.) -78 deg C, 10 min, 2.) -78 deg C to room temperature, 3 h<br />4: 93 percent / potassium hydroxide / ethanol / 4 h<br />5: 87 percent / conc. HCl / dioxane; methanol / 1.5 h / Ambient temperature<br />6: 92 percent / 30percent H₂O₂, 5percent NaOH / dioxane; methanol / 3 h / Ambient temperature<br />7: 1.) boron trifluoride etherate, 2.) sodium borohydride / 1.) benzene, 20 min, 2.) THF, room temperature, 2 h<br />8: 66 percent / hydrogen / 10percent Pd/C / methanol<br /> <br /> &nbsp;