Ethanol → Ethyl 2-furoate

HRID 1184948Notes

Reaction equation

HRID 1184948 reaction equation
[CH2:1](O)[CH3:2].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([OH:11])=[O:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([O:11][CH2:1][CH3:2])=[O:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 69192-Furancarboxylic acidHCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 11980Ethyl 2-furoateYield 88.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (100 ml), ethanol (12.33 g, 267.67 mmol) and 2-furancarboxylic acid (25 g, 223.05 mmol) were added into a 200-ml flask in this order at room temperature and then p-toluenesulfonic acid monohydrate (6.65 g, 34.96 mmol) was charged thereto. The solution was gently heated and subjected to reflux dehydration for 3 to 5 hours. After reflux dehydration, the solution was cooled to around room temperature, added with triethylamine (5.64 g, 55.76 mmol) at room temperature, stirred and then added with silica gel. After stirring for a while, the silica gel was filtered off. After the solvent of the filtrate was removed in vacuum distillation, ethyl 2-furancarboxylate (27.60 g, 88%) was isolated in distillation.

Workup

  1. temperatureThe solution was gently heated
  2. temperatureto reflux dehydration for 3 to 5 hours
  3. temperatureAfter reflux dehydration
  4. temperaturethe solution was cooled to around room temperature
  5. additionadded with silica gel
  6. stirringAfter stirring for a while
  7. filtrationthe silica gel was filtered off
  8. customAfter the solvent of the filtrate was removed in vacuum distillation

Sources & evidence

ORD record
ord-11fb6d94b99c41e7932ca24dd410186e
Source dataset
uspto-grants-2014_03
Patent number
US08669375B2

Reaction notes

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