Acetone → HCID 19419334, compound

HRID 864875Notes

Reaction equation

HRID 864875 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[C:4]=1[N+:10]([O-:12])=[O:11])[CH3:2].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CCOCC.[I-].[Na+]>[CH2:15]([O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[N+:10]([O-:12])=[O:11])[CH:14]=[CH2:13]

Participants

7

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 19419313HCID 19419313, compound

Product 1

HCID 19419334HCID 19419334, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture consisted of 3.15 g (18.2 mmol) of 2-ethyl-6-hydroxy-1-nitrobenzene, 4.44 g (36.7 mmol) of allyl bromide, 2.70 g (19.5 mmol) of potassium carbonate, 262 mg (1.75 mmol) of sodium iodide and 30 ml of acetone was heated under refluxing for 2 hours. After cooling, the reaction mixture was diluted with ether and the diluted mixture was filtered to remove inorganic substances. The filtrate was concentrated and the concentrate was purified by column chromatography through 150 g of silica gel using a 1:9 mixture of ether and hexane as an eluent to give 3.68 g (98%) of the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 2 hours
  3. temperatureAfter cooling
  4. filtrationthe diluted mixture was filtered
  5. customto remove inorganic substances
  6. concentrationThe filtrate was concentrated
  7. customthe concentrate was purified by column chromatography through 150 g of silica gel using
  8. additiona 1:9 mixture of ether and hexane as an eluent

Sources & evidence

ORD record
ord-1a5de8ac46664529bd22820dd85c2dce
Source dataset
uspto-grants-1996_10
Patent number
US05563169

Reaction notes

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