Acetic Acid → 1-(2,4-Dihydroxy-5-isobutyl-phenyl)-ethanone

HRID 646511Notes

Reaction equation

HRID 646511 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[OH:12])[CH:2]([CH3:4])[CH3:3].[C:13](O)(=[O:15])[CH3:14].CC([O-])=O.[Na+]>B(F)(F)F>[OH:11][C:8]1[CH:7]=[C:6]([OH:12])[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][C:9]=1[C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 139510854-Isobutylresorcinol

Product 1

HCID 592647801-(2,4-Dihydroxy-5-isobutyl-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 6356Boron trifluorideSolvent

Conditions

Temperature
90 °C

Procedure

4-Isobutyl-benzene-1,3-diol (1 eq)was taken up in BF3.Oet2 (6 eq) and aceticacid (2 eq) was added. The solution was heated for 16 hours at 90° C. than allowed to cool to room temperature. The solution was added drop wise to 10% NaOAc (aq) and allowed to stand for 4 hours, before being extracted twice with diethyl ether. The organic phases were combined and washed with sat. NaHCO3 (aq), then dried over magnesium sulfate, filtered and concentrated in vacuo to give 1-(2,4-dihydroxy-5-isobutyl-phenyl)-ethanone, which was used without additional purification.

Workup

  1. temperatureto cool to room temperature
  2. extractionbefore being extracted twice with diethyl ether
  3. washwashed with sat. NaHCO3 (aq)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-932f18fd852d41a18dd0b27a9bbd0d55
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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