1: ethyl 2,4-dimethoxy-6-methylbenzoate With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 0.5 h; 2: acetaldehyde in tetrahydrofuran T=-78 - 20°C; 2 h; 3: With ethanol in tetrahydrofuran

sodium tetrahydroborate in methanol T=20°C; 10 h;

1: 74 percent / propionic anhydride / 15 h / 155 - 160 °C 2: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 20 h / 1551.4 Torr 3: 88 percent / polyphosphoric acid (PPA) / 0.2 h / 90 °C 4: 88 percent / 1.5 h / Ambient temperature 5: 61 percent / O3 / ethyl acetate / 15 h / -55 °C 6: H2 / 10percent Pd/C View Scheme

hydrogenchloride in propan-1-ol 144 h; Heating;

1: 98 percent / K2CO3 / acetone / Heating 2: 1.) LDA, 2.) acetaldehyde / 1.) THF, hexane-78 deg C, 30 min, 2.) THF, hexane, a.) -78deg C, 1 h, b.) RT, overnight View Scheme

1: 67 percent / pyridine / tetrahydrofuran / 1.) room temperature, 40 min, 2.) reflux, 1 h 2: 91 percent / 0.17 h / 140 - 150 °C 3: 70 percent / sodium borohydride / 1 h / Heating View Scheme

1: 1.) LDA / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) -78 deg C-room temperature, 4 h 2: 81 percent / water / 16 h 3: 91 percent / acetyl chloride / 0.5 h / Heating 4: 67 percent / pyridine / tetrahydrofuran / 1.) room temperature, 40 min, 2.) reflux, 1 h 5: 91 percent / 0.17 h / 140 - 150 °C 6: 70 percent / sodium borohydride / 1 h / Heating View Scheme

1: 81 percent / water / 16 h 2: 91 percent / acetyl chloride / 0.5 h / Heating 3: 67 percent / pyridine / tetrahydrofuran / 1.) room temperature, 40 min, 2.) reflux, 1 h 4: 91 percent / 0.17 h / 140 - 150 °C 5: 70 percent / sodium borohydride / 1 h / Heating View Scheme

1: 2.) D2O / 1.) -78 deg C, THF, 1 h 2: 1.) lithium di-isopropylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C View Scheme

anhydrous sodium borate; sodium carbonate anschliessend ansaeuern;