Benzyl Bromide → 1-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-ethanone

HRID 646512Notes

Reaction equation

HRID 646512 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([O:1][C:2]1[CH:7]=[C:6]([O:8][CH2:13][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[C:5]([CH2:9][CH:10]([CH3:11])[CH3:12])=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 592647801-(2,4-Dihydroxy-5-isobutyl-phenyl)-ethanone

Product 1

HCID 247746071-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

1-(2,4-Dihydroxy-5-isobutyl-phenyl)-ethanone (1 eq) was dissolved in DMF and potassium carbonate (4.4 eq) then benzyl bromide (4.4 eq) was added. The suspension was heated, with stirring to 150° C., under nitrogen, for 16 hrs. The solution was cooled to room temperature, filtered and concentrated to dryness. This solid was purified column chromatography (silica, hexanes:ethyl aceate 4:1) then re-crystallised from ethyl acetate:hexanes to give 1-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-ethanone as colourless crystals.

Workup

  1. temperatureThe suspension was heated
  2. temperatureThe solution was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThis solid was purified column chromatography (silica, hexanes:ethyl aceate 4:1)
  6. customthen re-crystallised from ethyl acetate

Sources & evidence

ORD record
ord-cdb62e05719b4123b74678a06c368a60
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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