in tetrahydrofuran

1: thionyl chloride / 16.25 h / 0 °C / Reflux 2: acetonitrile / 12 h / Reflux 3: 5 Pd(II)/C(eggshell); hydrogen / ethanol / 8 h / 20 °C / 7500.75 Torr View Scheme

in water; acetonitrile

1: With anhydrous phosphorous acid; phosphorus trichoride T=60 - 75°C; 9 h; 2: With water T=25 - 95°C; 8 h;

1: in water T=0 - 80°C; 1 h; 2: With water 6 h; Heating / reflux;

in hydrogenchloride; anhydrous phosphorus trichloride; ethanol; water; chlorobenzene

1.1: sulfuric acid / 6 h / Reflux 2.1: tert.-butylnitrite; sodium ethanolate / ethanol / 20 h 2.2: 1 h 3.1: formic acid; zinc / methanol; water / 15 h / 0 - 4 °C 4.1: dichloromethane / 0 - 20 °C 5.1: water; potassium hydroxide / ethanol / 18 h / 20 °C View Scheme

1: thionyl chloride / 16.25 h / 0 °C / Reflux 2: acetonitrile / 12 h / Reflux 3: 5 Pd(II)/C(eggshell); hydrogen / ethanol / 8 h / 20 °C / 7500.75 Torr 4: (R)-(-)-α-hydroxybenzeneacetic acid / ethyl acetate / 4 h / Reflux; Resolution of racemate View Scheme

1: thionyl chloride / 16.25 h / 0 °C / Reflux 2: acetonitrile / 12 h / Reflux 3: 5 Pd(II)/C(eggshell); hydrogen / ethanol / 8 h / 20 °C / 7500.75 Torr 4: (S)-α-hydroxybenzeneacetic acid / ethyl acetate / 4 h / Reflux; Resolution of racemate 5: hydrogenchloride / diethyl ether / 2 h / 0 °C View Scheme

1: SOCl2 2: LiAlH4 3: mCPBA 4: Me2NCOCl / CH2Cl2 5: methanol 6: CH2Cl2 7: 70 percent / KH / CH2Cl2 / Ambient temperature 8: 1) BF3 * MeOH, 2) NaBH4 / 1) 120 deg C 9: imidazole 10: 1) O3, 2) NaH / 1) methanol, -78 deg C, 2) CH2Cl2, -78 deg C 11: MsCl, Et3N 12: CSA / ethanol 13: Dess-Martin periodinane (DMP) 14: 2) Dess-Martin periodinane (DMP) / 1) irradiation, toluene, -78 deg C 15: 98 percent / methanol 16: Dess-Martin periodinane (DMP) 17: NaClO2, NaH2PO4 / various solvent(s) 19: 1) HCO2H, 2) H2O / 2) 140 deg C 20: 3 N KOH / 120 °C View Scheme