Resorcinol → 1-(2,4-dihydroxyphenyl)-3-methylbutan-1-one

HRID 2355260Notes

Reaction equation

HRID 2355260 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH:3]([CH3:5])[CH3:4].[C:8]1([CH:15]=[CH:14][CH:13]=[C:11]([OH:12])[CH:10]=1)[OH:9].B(F)(F)F.CCOCC.C([O-])(=O)C.[Na+]>>[OH:9][C:8]1[CH:10]=[C:11]([OH:12])[CH:13]=[CH:14][C:15]=1[C:1](=[O:7])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 4

HCID 5054ResorcinolHCID 8000Boron trifluoride etherateHCID 10430Isovaleric AcidHCID 517045Sodium Acetate

Product 1

HCID 8194681-(2,4-dihydroxyphenyl)-3-methylbutan-1-oneYield 111.2%

Conditions

Temperature
90 °C

Procedure

Add isovaleric acid (5.10 g, 50 mmol, 5.5 mL) in one portion to a mixture of resorcinol (5.00 g, 45.4 mmol) in boron trifluoride etherate (38.67 g, 272.5 mmol, 34.5 mL) at room temperature under Argon gas. Heat the reaction mixture at 90° C. for 1.5 hr. Cool the reaction to room temperature and pour it into a 20% aqueous sodium acetate solution and stir overnight. Extract the aqueous mixture with ethyl acetate (3×). Combine the organic layers, wash with saturated aqueous sodium bicarbonate solution and brine sequentially. Dry the organic phase over sodium sulfate, filter and concentrate under reduced pressure to provide the product as a brownish oil (9.80 g; 50.5 mmol, 111% yield). MS (m/z): 195 (M+1).

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. extractionExtract the aqueous mixture with ethyl acetate (3×)
  4. washCombine the organic layers, wash with saturated aqueous sodium bicarbonate solution and brine sequentially
  5. dry with materialDry the organic phase over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-864ff58690914249b64e1da539208629
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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