Water → (2S)-3-Phenylpropane-1,2-diol

HRID 223788

Reaktionsgleichung

Reaktionsgleichung von HRID 223788
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C@:13](C)(O)[C:14]([OH:16])=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+].[O:22]1CCC[CH2:23]1>>[OH:22][CH2:23][C@@H:14]([OH:16])[CH2:13][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 445144(S)-Atrolactic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 446127(2S)-3-Phenylpropane-1,2-diol

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureunder reflux
  2. temperatureafter cooling
  3. waitboiled for 0.5 hour
  4. temperatureunder reflux
  5. filtrationThe white precipitate was filtered off
  6. washcarefully washed with hot THF
  7. distillationThe solvent was distilled off from the combined filtrates
  8. distillationthe crude product fractionally distilled

Quellen und Nachweise

ORD-Eintrag
ord-563f43a0cf5b4d88ab3500786c92f5d4
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04356324

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