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

HRID 1891183Notes

Reaction equation

HRID 1891183 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 acetate 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 acetate 4:1)
  6. customthen re-crystallised from ethyl acetate

Sources & evidence

ORD record
ord-87af5240e9864151b6a048ff48d811e8
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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