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

HRID 275058

Reaction equation

HRID 275058 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]1

Participants

5

Reactant 2

HCID 6506Triethyl CitrateHCID 178418361HCID 178418361, compound

Product 2

HCID 2773573(Oxan-4-yl)methanolYield 1%HCID 111262252-(Oxolan-3-yl)ethan-1-olYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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

  1. customwere hydrogenated at 200° C.
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-86f587d5a01442c69df9ee015b0d18fc
Source dataset
uspto-grants-1995_02
Patent number
US05391771

Linked notes

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