Water → HCID 22607842, compound

HRID 46439Notes

Reaction equation

HRID 46439 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

HCID 962WaterHCID 18898IsomaltolHCID 24819Phosphorus pentachloride

Product 1

HCID 22607842HCID 22607842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. customto come to room temperature
  2. customthe CH2Cl2 layer separated
  3. extractionThe aqueous layer was then extracted with CH2Cl2
  4. concentrationconcentrated
  5. 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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