Triethyl Citrate → 1,2,3-Triethyl 1,2,3-propanetricarboxylate

HRID 275061

Reaction equation

HRID 275061 reaction equation
[C:1]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:2][C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:5]([O:7][CH2:8][CH3:9])=[O:6])O.O1CCCC1.[H][H]>C(O)C>[CH2:2]([C:1]([O:17][CH2:18][CH3:19])=[O:16])[CH:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 6506Triethyl CitrateHCID 8028TetrahydrofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 2210551,2,3-Triethyl 1,2,3-propanetricarboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

400 ml of triethyl citrate were hydrogenated at 175° C. and 10 bar together with 1100 ml of tetrahydrofuran and 60 g of catalyst G (4-mm tablets) until the take-up of hydrogen had ceased. The reaction product was freed from ethanol and distilled under reduced pressure, giving 193 g (45%) of triethyl propane-1,2,3-tricarboxylate.

Workup

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

Sources & evidence

ORD record
ord-fdfd6c8e013d482092b9552ae9442a80
Source dataset
uspto-grants-1995_02
Patent number
US05391771

Linked notes

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