Water → HCID 22607842, compound
Reaction equation
[CH3:1][C:2]([C:4]1[O:8][CH:7]=[CH:6][C:5]=1O)=[O:3].P(Cl)(Cl)(Cl)(Cl)[Cl:11].O>C(Cl)Cl>[C:2]([C:4]1[O:8][CH:7]=[CH:6][C:5]=1[Cl:11])(=[O:3])[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Isomaltol (6.3 g, 0.05 moles) in 60 ml of CH2Cl2 was added dropwise over 10 minutes to a solution of PCl5 (10.4 g, 0.05 moles) in 125 ml of CH2Cl2 at 4° C. After stirring at 4°-5° C. for 1 hour, the reaction was allowed to come to room temperature, poured into 350 ml of water and the CH2Cl2 layer separated. The aqueous layer was then extracted with CH2Cl2, the CH2Cl2 layers combined and then concentrated to yield a dark oil, 7.0 g. Pure 2-acetyl-3-chloro-furan was obtained by chromatography from silica gel, NMR (CDCl3, δ) 7.5 (1H, d, J=2Hz), 6.56 (1H, d, J=2Hz), 2.53 (3H, s).
Workup
- customto come to room temperature
- customthe CH2Cl2 layer separated
- extractionThe aqueous layer was then extracted with CH2Cl2
- concentrationconcentrated
- customto yield a dark oil, 7.0 g
Sources & evidence
- ORD record
- ord-0ef49ee81cee40e2bf8c44ec76e31cea
- Source dataset
- uspto-grants-1979_11
- Patent number
- US04173572
Reaction notes
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