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5-Chloromethylfurfural → 5-Acetoxymethyl-2-furaldehyde

HRID 1051033
Notes
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Reaction equation

HRID 1051033 reaction equation
Cl[CH2:2][C:3]1[O:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[C:10]([O-:13])(=[O:12])[CH3:11].C([N+]1C=CN(C)C=1)C>CC#N>[C:10]([O:13][CH2:2][C:3]1[O:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)(=[O:12])[CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 741915-Chloromethylfurfural2×HCID 178476379HCID 178476379, compound

Product 1

HCID 663495-Acetoxymethyl-2-furaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a round flask, 2 mL of methyl cyanide (acetonitrile) as an organic solvent was introduced, 0.145 g (1 mmol) of 5-chloromethylfurfural (CMF, compound I) was dissolved in the organic solvent, 0.170 g (1 mmol) of 1-ethyl-3-methylimidazolium acetate was added to the solution, and then the mixed solution was reacted at normal pressure and room temperature for 5 minutes. After the reaction, the reaction product was extracted by the addition of a small amount of water (5 mL) and ethyl acetate (added twice by 20 mL) to obtain an organic layer. The obtained organic layer was concentrated under reduced pressure to obtain light yellow liquid 5-acetoxymethylfurfural (AcHMF, compound II). The yield thereof is 36%.

Workup

  1. additionwas added to the solution
  2. customthe mixed solution was reacted at normal pressure and room temperature for 5 minutes
  3. customAfter the reaction
  4. extractionthe reaction product was extracted by the addition of a small amount of water (5 mL) and ethyl acetate (
  5. additionadded twice by 20 mL)
  6. customto obtain an organic layer
  7. concentrationThe obtained organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa13fc02b128447c81c9ce0551e8f51c
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09388150B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes