Carbon Tetrachloride → 2-(5-Chloropentyl)-5-acetylfuran

HRID 1723348Notes

Reaction equation

HRID 1723348 reaction equation
[C:1]([C:4]1[O:8][C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:35]>>[Cl:35][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:7]1[O:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 103303035-(5-Acetyl-2-furanyl)pentanol

Product 1

HCID 103532152-(5-Chloropentyl)-5-acetylfuranYield 60%

Procedure

5-(5-Acetyl-2-furanyl)pentanol (9.8 g), 13.1 g of triphenylphosphine and 100 ml of carbon tetrachloride were combined and heated at reflux for 4 hours. The reaction mixture was concentrated in vacuo, and the residue was dissolved in ether and filtered. The filtrate was concentrated and the residue distilled twice to give 2-(5-chloropentyl)-5-acetylfuran, b.p. 100°-102° C. (0.05 mm) in 60% yield.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in ether
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. distillationthe residue distilled twice

Sources & evidence

ORD record
ord-76cedab43c394c8180bbc60409b1dfe0
Source dataset
uspto-grants-1989_08
Patent number
US04861791

Reaction notes

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