Resorcinol → 1-(2,4-Dihydroxyphenyl)-2-methylpropan-1-one

HRID 1891180Notes

Reaction equation

HRID 1891180 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].B(F)(F)F.CCOCC.[C:18](O)(=[O:22])[CH:19]([CH3:21])[CH3:20].CC([O-])=O.[Na+]>>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[C:18](=[O:22])[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 4

HCID 5054ResorcinolHCID 6590Isobutyric AcidHCID 8000Boron trifluoride etherateHCID 517045Sodium Acetate

Product 1

HCID 159157311-(2,4-Dihydroxyphenyl)-2-methylpropan-1-one

Conditions

Temperature
90 °C

Procedure

Resorcinol (1 eq) was taken up in BF3.OEt2 (6 eq) and isobutyric acid (1 eq) added. The solution was heated for 1.5 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 in to EtOAc. 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-phenyl)-2-methyl-propan-1-one as a red oil which was used without additional purification

Workup

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

Sources & evidence

ORD record
ord-edf48e7c06f249e5815d3a23434ea5f2
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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