Acetyl chloride → 5-Acetoxymethyl-2-furaldehyde

HRID 1654105

Reaction equation

HRID 1654105 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH2:6][C:7]1[O:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=1.P([O-])(O)(O)=O.[Na+]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([O:5][CH2:6][C:7]1[O:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 2373325-(Hydroxymethyl)furfuralHCID 23672064Monosodium phosphate

Product 1

HCID 663495-Acetoxymethyl-2-furaldehyde

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

10.05 ml of acetyl chloride were added at 5° C. to a solution of 16.2 g of 5-hydroxymethyl-2-furancarboxaldehyde and 200 ml of methylene chloride and 11.4 ml of pyridine and 50 ml of methylene chloride were then added. The reaction mixture was stirred for 3 hours at 20° C. and the reaction mixture was treated with an aqueous sodium dihydrogenphosphate solution and extracted with methylene chloride. The extract was dried and concentrated to obtain 19.35 g of the desired product after chromatography on silica by eluting with a hexane/ethyl acetate (7/3) mixture.

Workup

  1. additionwere then added
  2. extractionextracted with methylene chloride
  3. customThe extract was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b7b9fe9f14154908a8e4556b0d8d9b01
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Linked notes

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