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

HRID 2097297Notes

Reaction equation

HRID 2097297 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].B(F)(F)F.[CH3:17][CH2:18][O:19]CC.C(O)(=O)C.CC([O-])=O.[Na+]>>[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:18](=[O:19])[CH3:17]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 517045Sodium AcetateHCID 139510854-Isobutylresorcinol

Product 1

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

Conditions

Temperature
90 °C

Procedure

4-Isobutyl-benzene-1,3-diol (1 eq) was taken up in BF3.OEt2 (6 eq) and acetic acid (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-61cd99a26c8b41a88026c030debdb936
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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