Sodium hydride → 1-[3-(3,3-Dimethylbutoxy)-5-methoxyphenyl]ethanone

HRID 657958Notes

Reaction equation

HRID 657958 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.I[CH2:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17].[H-].[Na+]>CN(C=O)C.CC(=O)OCC>[CH3:17][C:16]([CH3:19])([CH3:18])[CH2:15][CH2:14][O:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 148248991-Iodo-3,3-dimethylbutaneHCID 193506661-(3-Hydroxy-5-methoxyphenyl)ethanone

Product 1

HCID 580459821-[3-(3,3-Dimethylbutoxy)-5-methoxyphenyl]ethanoneYield 50.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Hydroxy-5-methoxyphenyl)ethanone (O3.033; 1.12 g) and 1-iodo-3,3-dimethylbutane (1.57 g) were dissolved in DMF, and sodium hydride (194 mg) was added. After stirring at RT for 2 h, the DMF was drawn off. The residue was taken up in EA, washed with water, dried, filtered and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA 0-50% within 30 min). 850 mg of the title compound were obtained.

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customsilica gel (40 g cartridge, n-heptane/EA 0-50% within 30 min)

Sources & evidence

ORD record
ord-09951ff0eae8488e994cde1d2f7dba82
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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