Multi-step reaction with 12 steps
1.1: 89 percent / conc. H2SO4 / 16 h / Heating
2.1: 82 percent / Et3N / CH2Cl2 / 16 h / 20 °C
3.1: 88 percent / 1,2-dichloro-benzene / 3 h / 180 °C
4.1: KOH; H2O / methanol / 2 h / Heating
5.1: 0.81 g / 1 h / 20 °C
6.1: 96 percent / MCPBA / CH2Cl2 / 2 h / 20 °C
7.1: H2 / Pd/C / ethanol / 3102.97 Torr
8.1: tetrahydrofuran / -20 °C
9.1: BH3*DMS / tetrahydrofuran / 20 °C
10.1: 37 percent / tetrahydrofuran / Heating
11.1: 95 percent / NaOH; H2O / methanol / 20 °C
12.1: CDI / dimethylformamide / 50 °C
12.2: 73 percent / dimethylformamide / 20 °C
With
potassium hydroxide; sodium hydroxide; dimethylsulfide borane complex; sulfuric acid; water; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1'-carbonyldiimidazole;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene;
1.1: Esterification / 2.1: Substitution / 3.1: Rearrangement / 4.1: Hydrolysis / 5.1: Methylation / 6.1: Oxidation / 7.1: Reduction / 8.1: Formylation / 9.1: Reduction / 10.1: Acylation / 11.1: Hydrolysis / 12.1: Addition / 12.2: Substitution;
DOI:10.1039/b000135j