Butyl iodide → HCID 22678123, compound

HRID 1837551Notes

Reaction equation

HRID 1837551 reaction equation
[CH2:1](I)[CH2:2][CH2:3][CH3:4].[C:6]([C:9]1[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:12]([OH:19])=[CH:11][CH:10]=1)(=[O:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:6]([C:9]1[CH:10]=[CH:11][C:12]([O:19][CH2:1][CH2:2][CH2:3][CH3:4])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 10962Butyl iodide2×HCID 11430Potassium Carbonate2×HCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 22678123HCID 22678123, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

n-Butyl iodide (13.2 ml, 117 mmol) was added to a mixture of methyl 5-acetylsalicylate (15 g, 77 mmol) and potassium carbonate (16 g, 117 mmol) in acetonitrile (500 ml), and the reaction stirred at 60° C. for 18 hours. TLC analysis showed starting material remaining, so additional n-butyl iodide (26.4 ml, 234 mmol) and potassium carbonate (16 g, 117 mmol) were added and the reaction stirred at 60° C. for a further 72 hours. The cooled mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The phases were separated, the organic layer washed with brine, dried (MgSO4) and evaporated under reduced pressure to afford the title compound as a yellow oil that crystallised on drying in vacuo, 17.4 g.

Workup

  1. stirringthe reaction stirred at 60° C. for a further 72 hours
  2. concentrationThe cooled mixture was concentrated under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe phases were separated
  5. washthe organic layer washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4cfc2bf4c9f04305b6187fa7fb7ae3e1
Source dataset
uspto-grants-2004_08
Patent number
US06784185B2

Reaction notes

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