Acetone → HCID 54533151, compound

HRID 1380075Notes

Reaction equation

HRID 1380075 reaction equation
[OH:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20](=[O:23])([O-])[O-:21].[K+].[K+].C[C:27](C)=[O:28]>>[N+:9]([C:3]1[C:2]([O:1][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:8][C:27](=[O:28])[C:20]([OH:21])=[O:23])([O-:11])=[O:10]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 210263-Methyl-2-nitrophenol

Product 1

HCID 54533151HCID 54533151, compound

Procedure

A solution of 50 g. 3-hydroxy-2-nitrotoluene (Pfaltz & Bauer, NO9200), and 30 ml benzyl bromide in acetone is treated with excess potassium carbonate and refluxed for 21/2 hours. The reaction is filtered and the solvent is removed in vacuo. The resulting ether is distilled. This compound (24 g.) is added to a solution of potassium ethoxide (4 g. potassium in ethanol) in ethyl ether (350 ml) and refluxed for 18 hours. The solvent is removed in vacuo and the remaining oil is treated with 1N NaOH at room temperature for 1 hour. The mixture is washed with ether (twice), acidified with hydrochloric acid yielding the desired product.

Workup

  1. temperaturerefluxed for 21/2 hours
  2. filtrationThe reaction is filtered
  3. customthe solvent is removed in vacuo
  4. distillationThe resulting ether is distilled
  5. additionThis compound (24 g.) is added to a solution of potassium ethoxide (4 g. potassium in ethanol) in ethyl ether (350 ml)
  6. temperaturerefluxed for 18 hours
  7. customThe solvent is removed in vacuo
  8. additionthe remaining oil is treated with 1N NaOH at room temperature for 1 hour
  9. washThe mixture is washed with ether (twice),

Sources & evidence

ORD record
ord-b7314172399b4fe5a8bd2dd94501b4c9
Source dataset
uspto-grants-1986_04
Patent number
US04579865

Reaction notes

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