1,6-hexanedioic acid T=190°C; 6 h;

2: 1) NaH / 1) allylalcohol, mineral oil, 90 deg C, 3 h; 2) 100 deg C, 3-4 h 3: 85 percent Chromat. / Pd(OAc)2, PPh3 / acetonitrile / 0.5 h / 80 °C / Heating; effect and amount of different catalyst and solvent 4: 95 percent / H2 / Lindlar catalyst / butan-1-ol / 2 h / 760 Torr / Ambient temperature 5: NaOMe / methanol / 10 h / 0 °C View Scheme

1: 1) NaH / 1) allylalcohol, mineral oil, 90 deg C, 3 h; 2) 100 deg C, 3-4 h 2: 85 percent Chromat. / Pd(OAc)2, PPh3 / acetonitrile / 0.5 h / 80 °C / Heating; effect and amount of different catalyst and solvent 3: 95 percent / H2 / Lindlar catalyst / butan-1-ol / 2 h / 760 Torr / Ambient temperature 4: NaOMe / methanol / 10 h / 0 °C View Scheme

1: 95 percent / H2 / Lindlar catalyst / butan-1-ol / 2 h / 760 Torr / Ambient temperature 2: NaOMe / methanol / 10 h / 0 °C View Scheme

1: 85 percent Chromat. / Pd(OAc)2, PPh3 / acetonitrile / 0.5 h / 80 °C / Heating; effect and amount of different catalyst and solvent 2: 95 percent / H2 / Lindlar catalyst / butan-1-ol / 2 h / 760 Torr / Ambient temperature 3: NaOMe / methanol / 10 h / 0 °C View Scheme

sodium methylate in methanol T=0°C; 10 h; Yield given;

2: 1) NaH / 1) allylalcohol, mineral oil, 90 deg C, 3 h; 2) 100 deg C, 3-4 h 3: 55 percent Chromat. / Pd(OAc)2, bis(diphenylphosphino)ethane / acetonitrile / Heating 4: NaOMe / methanol / 10 h / 0 °C View Scheme

1: 1) NaH / 1) allylalcohol, mineral oil, 90 deg C, 3 h; 2) 100 deg C, 3-4 h 2: 55 percent Chromat. / Pd(OAc)2, bis(diphenylphosphino)ethane / acetonitrile / Heating 3: NaOMe / methanol / 10 h / 0 °C View Scheme

1: 55 percent Chromat. / Pd(OAc)2, bis(diphenylphosphino)ethane / acetonitrile / Heating 2: NaOMe / methanol / 10 h / 0 °C View Scheme