Citric Acid → 2-(Oxolan-3-yl)ethan-1-ol

HRID 275056Notes

Reaction equation

HRID 275056 reaction equation
[C:1]([OH:13])(=O)[CH2:2][C:3]([CH2:8][C:9]([OH:11])=O)([C:5]([OH:7])=O)O.[H][H].C(O)C>C(O)CCC>[OH:11][CH2:9][CH2:8][CH:3]1[CH2:2][CH2:1][O:13][CH2:5]1.[OH:7][CH2:5][CH:3]1[CH2:2][CH2:1][O:13][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 702EthanolHCID 178418361HCID 178418361, compound

Product 2

HCID 2773573(Oxan-4-yl)methanolYield 1.5%HCID 111262252-(Oxolan-3-yl)ethan-1-olYield 52%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

400 g of citric acid were dissolved in 1000 ml of n-butanol and hydrogenated at 250° C. and 200 bar together with 60 g of catalyst A (4-mm pellets) until the take-up of hydrogen had ceased. The reaction product was freed from n-butanol and ethanol and distilled under reduced pressure, giving 99 g (52%) of 3-(2'-hydroxyethyl)tetrahydrofuran and 2.9 g (1.5%) of 4-hydroxymethyltetrahydropyran.

Workup

  1. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-8855e12654a647c08c93ecb4637923f7
Source dataset
uspto-grants-1995_02
Patent number
US05391771

Reaction notes

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