Diethylene Glycol → 2-Butyl-5-chloro-1-benzofuran

HRID 1283655Notes

Reaction equation

HRID 1283655 reaction equation
[C:1]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:9]=2[CH:10]=1)(=O)[CH2:2][CH2:3][CH3:4].NN.C(O)COCCO.[OH-].[K+]>O>[CH2:1]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:9]=2[CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 215104891-(5-Chloro-1-benzofuran-2-yl)butan-1-one

Product 1

HCID 138150732-Butyl-5-chloro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 31.5 g. (0.14 mol.) of 2-butyryl-5-chlorobenzofuran and 35 ml. of 98% hydrazine in 70 ml. of diethylene glycol was warmed for a few minutes on a steam bath. Then 23.3 g. of potassium hydroxide was added and the reaction mixture was refluxed for two hours. After cooling, water was added to the mixture and the resulting aqueous solution was extracted with benzene. The extract was washed with water, 10% aqueous hydrochloric acid and water, dried (MgSO4) and concentrated in vacuo to yield 2-n-butyl-5-chlorobenzofuran, b.p. 70°-75° (10-15 mm.).

Workup

  1. additionA mixture of 31.5 g
  2. temperaturethe reaction mixture was refluxed for two hours
  3. temperatureAfter cooling
  4. extractionthe resulting aqueous solution was extracted with benzene
  5. washThe extract was washed with water, 10% aqueous hydrochloric acid and water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-026b91de298840b9855cd8b147cb307c
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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