Triethyl Citrate → 2-(Oxolan-3-yl)ethan-1-ol

Reaktionsgleichung

C(OCC)(=O)C[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=O)([C:5]([O:7][CH2:8][CH3:9])=O)O.O1CCCC1.[H][H]>C(O)C>[OH:7][CH2:5][CH2:3][CH:10]1[CH2:15][CH2:14][O:13][CH2:11]1.[OH:13][CH2:11][CH:10]1[CH2:9][CH2:8][O:7][CH2:5][CH2:3]1

Komponenten

Edukt 3

HCID 6506Triethyl Citrate

HCID 8028Tetrahydrofuran2×

HCID 178418361HCID 178418361, Verbindung

Produkt 2

HCID 2773573(Oxan-4-yl)methanolAusbeute 3,6 %

HCID 111262252-(Oxolan-3-yl)ethan-1-olAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

Versuchsvorschrift

400 ml of triethyl citrate were hydrogenated at 225° C. and 200 bar together with 1100 ml of tetrahydrofuran and 60 g of catalyst H (3-mm tablets) until the take-up of hydrogen had ceased. The reaction product was freed from tetrahydrofuran and ethanol and distilled under reduced pressure, giving 93.6 g (49%) of 3-(2'-hydroxyethyl)tetrahydrofuran and 6.8 g (3.6%) of 4-hydroxymethyltetrahydropyran.