Butyl iodide → HCID 19010813, compound

HRID 1741837Notes

Reaction equation

HRID 1741837 reaction equation
I[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:6][O:7][C:8]1[CH:16]=[C:15]([CH:17]=[C:18]([CH3:20])[CH3:19])[CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11]>C1C=CC=CC=1.CN(C)C=O.[Cu].[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:6][O:7][C:8]1[CH:16]=[C:15]([CH:17]=[C:18]([CH3:20])[CH3:19])[CH:14]=[CH:13][C:9]=1[C:10](=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 2

HCID 10962Butyl iodideHCID 190108112-Methoxy-4-(2-methyl-1-propen-1-yl)benzoyl chloride

Product 1

HCID 19010813HCID 19010813, compoundYield 60.1%

Reagents, catalysts & solvents 4

HCID 10290809Zinc copper coupleCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-iodobutane (185 mg) and zinc-copper couple (101 mg) in benzene (3 ml) and N,N-dimethylformamide (0.2 ml) was stirred at 60° C. for 2 hours. To the mixture, a solution of tetrakis(triphenylphosphine)palladium (31 mg) and 2-methoxy-4-(2-methyl-1-propenyl)benzoyl chloride (prepared from 138 mg of 2-methoxy-4-(2-methyl-1propenyl)benzoic acid and 0.07 ml of oxalyl chloride) in benzene (2 ml) was added, and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and the organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (9:1) to give 2'-methoxy-4'-(2-methyl-1-propenyl)valerophenone (91 mg) 10 as an oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel column
  9. washeluting with a mixture of hexane and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-083f3233553d4dbfa3c7d233603f8751
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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