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

HRID 493187Notes

Reaction equation

HRID 493187 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9](O)(=[O:13])[CH:10]([CH3:12])[CH3:11].B(F)(F)F>CC([O-])=O.[Na+]>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[C:9](=[O:13])[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 6356Boron trifluorideHCID 6590Isobutyric Acid

Product 1

HCID 159157311-(2,4-Dihydroxyphenyl)-2-methylpropan-1-oneYield 113.1%

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent

Procedure

Resorcinol (10.0 g, 91 mmol) and isobutyric acid (8.00 g, 1 eq.) were treated with BF3-etherate (68 mL, 6 eq.) and heated for 1.5 h to 90° C. After cooling the reaction mixture was carefully poured onto 500 mL of 10% aq. NaOAc solution, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness to leave 18.5 g of the title compound as light brown oil.

Workup

  1. temperatureheated for 1.5 h to 90° C
  2. temperatureAfter cooling the reaction mixture
  3. extractiontwofold extracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a94e8e7cdcdd4d02a09c677b9870aca8
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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