Methyl Ethyl Ketone → HCID 19829934, compound

HRID 1493630Notes

Reaction equation

HRID 1493630 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:11](I)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[CH2:11]([O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 125271-Iodohexane

Product 1

HCID 19829934HCID 19829934, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-nitrophenol (57.0 g, 0.41 mol), n-hexyliodide (87.0 g, 0.41 mol), potassium carbonate (57.0 g, 0.42 mol) and ethylmethylketone (300 ml) was heated at reflux for 18 h. Water (500 ml) was added and the mixture was extracted with ethyl acetate (2×500 ml). The combined extracts were washed with 8% aqueous sodium bicarbonate (2×250 ml) and brine (250 ml) and then dried (MgSO4) and evaporated to afford a dark brown liquid. Distillation under reduced pressure gave the ether (Intermediate 66) as a mobile yellow liquid (70.3 g, 77%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. extractionthe mixture was extracted with ethyl acetate (2×500 ml)
  4. washThe combined extracts were washed with 8% aqueous sodium bicarbonate (2×250 ml) and brine (250 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto afford a dark brown liquid
  8. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-95c920506ff04a92bd997a03771aca62
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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