Acetyl chloride → 5-Acetoxymethyl-2-furaldehyde
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.OP([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
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
10.05 cm3 of acetyl chloride is added at 5° C. to a solution containing 16.2 g of 5-(hydroxy methyl) 2-furan-carboxaldehyde and 200 cm3 of methylene chloride. Then 11.4 cm3 of pyridine and 50 cm3 of methylene chloride are added. The reaction mixture is maintained under agitation for 3 hours at 20° C. It is then treated with an aqueous solution of sodium acid phosphate and extracted with methylene chloride, followed by drying and concentrating. After chromatography on silica eluting with a hexane--ethyl acetate mixture (7-3), 19.35 g of desired product is obtained.
Workup
- extractionextracted with methylene chloride
- customby drying
- concentrationconcentrating
Sources & evidence
- ORD record
- ord-f2426e475fd047dbbbb6a664e51685ba
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05340835
Reaction notes
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