1: Phenylborneol With Sodium hydride in toluene 1 h; Heating / reflux; 2: 2-chloro-N,N-dimethylaminoethane in toluene 4 h; Heating / reflux;

1: Phenylborneol With sodium amide in 1,4-dioxane 2.5 h; Heating / reflux; 2: 2-chloro-N,N-dimethylaminoethane 4 h; Heating / reflux;

1.1: 73 percent / 630 °C / 0.02 - 0.03 Torr 2.1: H2SO4; HNO3 / -15 °C 2.2: 78 percent / H2SO4 / 0.25 h / 0 °C 3.1: 3-chlorobenzenecarboperoxoic acid (MCPBA); trifluoroacetic acid (TFA) / CH2Cl2 / 20 °C 4.1: LiOH / methanol; H2O / 20 °C 5.1: 99 percent / CrO3; H2SO4 / H2O; acetone / 30 h / 0 - 20 °C View Scheme