Triethyl Citrate → Ethyl tetrahydrofurfurylacetate

HRID 275060

Reaction equation

HRID 275060 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:6])O.[H][H].O1CCC[CH2:23]1>>[CH2:10]([CH2:3][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:11]1[O:13][CH2:14][CH2:15][CH2:23]1.[OH:7][CH2:5][CH2:3][CH:10]1[CH2:15][CH2:14][O:13][CH2:11]1

Participants

5

Reactant 3

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

Product 2

HCID 263175Ethyl tetrahydrofurfurylacetateYield 39%HCID 111262252-(Oxolan-3-yl)ethan-1-olYield 30%

Procedure

400 ml of triethyl citrate were hydrogenated at 175° C. and 50 bar together with 1100 ml of tetrahydrofuran and 60 g of catalyst F (4-mm tablets) until the take-up of hydrogen had ceased. The reaction product was freed from tetrahydrofuran and distilled under reduced pressure, giving 101 g (39%) of ethyl tetrahydrofurfurylacetate and 57 g (30%) of 3-(2'-hydroxyethyl)tetrahydrofuran.

Workup

  1. customwere hydrogenated at 175° C.
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-b5ff5c4a485e45258089b7c7e10d1743
Source dataset
uspto-grants-1995_02
Patent number
US05391771

Linked notes

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