(2S)-3-phenylpropane-1,2-diol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: There were dropped into a suspension of 50 grams of LiAlH4 in 750 ml of tetrahydrofuran (THF) cooled to 0° C. within 3 hours 83.1 grams of (S)-phenyl lactic acid dissolved in 250 ml of THF. The reaction mixture was boiled for 2 hours under reflux, after cooling treated portionwise with water and 43 ml of 4 N-NaOH and boiled for 0.5 hour under reflux. The white precipitate was filtered off and carefully washed with hot THF. The solvent was distilled off from the combined filtrates and the crude product fractionally distilled. There were obtained 64.6 grams of (S)-1,2-dihydroxy-3-phenyl-propane of boiling point 101°-102° C. (0.001 mbar). under reflux after cooling boiled for 0.5 hour under reflux The white precipitate was filtered off carefully washed with hot THF The solvent was distilled off from the combined filtrates the crude product fractionally distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: There were dropped into a suspension of 50 grams of LiAlH4 in 750 ml of tetrahydrofuran (THF) cooled to 0° C. within 3 hours 83.1 grams of (S)-phenyl lactic acid dissolved in 250 ml of THF. The reaction mixture was boiled for 2 hours under reflux, after cooling treated portionwise with water and 43 ml of 4 N-NaOH and boiled for 0.5 hour under reflux. The white precipitate was filtered off and carefully washed with hot THF. The solvent was distilled off from the combined filtrates and the crude product fractionally distilled. There were obtained 64.6 grams of (S)-1,2-dihydroxy-3-phenyl-propane of boiling point 101°-102° C. (0.001 mbar). under reflux after cooling boiled for 0.5 hour under reflux The white precipitate was filtered off carefully washed with hot THF The solvent was distilled off from the combined filtrates the crude product fractionally distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-2-hydroxy-3-phenylpropanoic acid (4.98 g, 30.0 mmol) in 100 mL of anhydrous THF was added slowly BH3.THF complex (90 mL, 1M in THF, 3.0 equiv.) with ice cooling under N2. The solution was stirred overnight at room temperature, and the reaction was quenched with water (Caution, copious H2 evolution). After evaporation of the solvent, the residue was diluted with water and extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford (S)-3-phenylpropane-1,2-diol (4.13 g, 91%) as a colorless oil. LC-MS (ESI) m/z 153 (M+H+). the reaction was quenched with water (Caution, copious H2 evolution) After evaporation of the solvent the residue was diluted with water extracted with EtOAc (3×50 mL) The combined organic layers were dried over Na2SO4 concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: There were dropped into a suspension of 50 grams of LiAlH4 in 750 ml of tetrahydrofuran (THF) cooled to 0° C. within 3 hours 83.1 grams of (S)-phenyl lactic acid dissolved in 250 ml of THF. The reaction mixture was boiled for 2 hours under reflux, after cooling treated portionwise with water and 43 ml of 4 N-NaOH and boiled for 0.5 hour under reflux. The white precipitate was filtered off and carefully washed with hot THF. The solvent was distilled off from the combined filtrates and the crude product fractionally distilled. There were obtained 64.6 grams of (S)-1,2-dihydroxy-3-phenyl-propane of boiling point 101°-102° C. (0.001 mbar). under reflux after cooling boiled for 0.5 hour under reflux The white precipitate was filtered off carefully washed with hot THF The solvent was distilled off from the combined filtrates the crude product fractionally distilled