1: 34 mg / 8 N Jones reagent / acetone / 0.08 h / 0 °C 2: 23 mg / diethyl ether 3: 40 percent / 38 percent NaOH, MeOH / 14 h / Heating View Scheme

With  lithium aluminium tetrahydride in  tetrahydrofuran T=0°C; 1 h;   

Multi-step reaction with 8 steps 1: 4.24 g / ethylenediammonium diacetate / propan-2-ol / 16 h / Ambient temperature2: 2.27 g / H2O / dioxane / 15 h / Heating3: 41 percent / BBr3 / CH2Cl2 / 1.) -40 deg C to 0 deg C, 1 h, 2.) 0 deg C, 30 min4: 83 percent / Et3N, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 25 h / Ambient temperature5: 97 percent / NaBH4 / propan-2-ol / 0.67 h / Heating6: 85 percent / 2 h / 270 °C7: 51 mg / K2CO3, methanol / 1 h / Ambient temperature8: 35.8 mg / 1 N n-Bu4NF / tetrahydrofuran / 0.67 h / Ambient temperature  

With  tetrabutyl ammonium fluoride in  tetrahydrofuran 0.666667 h;  Ambient temperature;   

Multi-step reaction with 5 steps 1: 83 percent / Et3N, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 25 h / Ambient temperature2: 97 percent / NaBH4 / propan-2-ol / 0.67 h / Heating3: 85 percent / 2 h / 270 °C4: 51 mg / K2CO3, methanol / 1 h / Ambient temperature5: 35.8 mg / 1 N n-Bu4NF / tetrahydrofuran / 0.67 h / Ambient temperature  

Multi-step reaction with 2 steps 1: 34 mg / 8 N Jones reagent / acetone / 0.08 h / 0 °C2: 23 mg / diethyl ether