Triethyl Citrate → 2-(Oxolan-3-yl)ethan-1-ol
Reaction equation
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.[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]1Participants
5
Reactant 2
Product 2
Reagents, catalysts & solvents 1
Procedure
400 ml of triethyl citrate were hydrogenated at 200° C. and 200 bar together with 1100 ml of ethanol and 60 g of catalyst B (4-mm pellets) until the take-up of hydrogen had ceased. The reaction product was freed from ethanol and distilled under reduced pressure, giving 80 g (42%) of 3-(2'-hydroxyethyl)tetrahydrofuran and 1.8 g (1%) of 4-hydroxymethyltetrahydropyran.
Workup
- customwere hydrogenated at 200° C.
- distillationdistilled under reduced pressure
Sources & evidence
- ORD record
- ord-86f587d5a01442c69df9ee015b0d18fc
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05391771
Reaction notes
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