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

HRID 275059

Reaction equation

HRID 275059 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.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

Participants

6

Reactant 3

HCID 6506Triethyl CitrateHCID 8028Tetrahydrofuran2×HCID 178418361HCID 178418361, compound

Product 2

HCID 2773573(Oxan-4-yl)methanolYield 3.6%HCID 111262252-(Oxolan-3-yl)ethan-1-olYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customwere hydrogenated at 225° C.
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-e0c800179a6a41f3800b0b39c6564e34
Source dataset
uspto-grants-1995_02
Patent number
US05391771

Linked notes

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