2',4',6'-Trihydroxyacetophenone → 1-[2,4,6-Trihydroxy-3,5-di(3-methyl-2-buten-1-yl)phenyl]ethanone

HRID 1528036

Reaction equation

HRID 1528036 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[C:3]=1[C:10](=[O:12])[CH3:11].[CH2:13](Br)[CH2:14][C:15]([CH3:17])=[CH2:16]>[OH-].[K+]>[OH:1][C:2]1[C:7]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[C:6]([OH:8])[C:5]([CH2:7][CH:2]=[C:3]([CH3:10])[CH3:4])=[C:4]([OH:9])[C:3]=1[C:10](=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 680732',4',6'-TrihydroxyacetophenoneHCID 5495854-Bromo-2-methylbut-1-ene

Product 1

HCID 109796271-[2,4,6-Trihydroxy-3,5-di(3-methyl-2-buten-1-yl)phenyl]ethanoneYield 38.7%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

1-(2,4,6-trihydroxyphenyl]ethanone (2.0 mg, 11.9 mmol) was dissolved in a 5% potassium hydroxide aqueous solution (20 mL). After the mixture was cooled below 0° C., isopentenyl bromide (3.6 g, 24 mmol) was slowly added dropwise within 30 min. The reaction mixture was stirred at room temperature for 2 hours, then poured into an ice water and acidified to pH 2. The reaction mixture was extracted with ethyl acetate. The extract was collected and dried over anhydrous sodium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography (dichloromethane as eluent) to give the desired compound (0.7 g, yield 20%).

Workup

  1. temperatureAfter the mixture was cooled below 0° C.
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. customThe extract was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was purified by silica gel column chromatography (dichloromethane as eluent)

Sources & evidence

ORD record
ord-3cb7b15b61034ec69b25282892b2f98a
Source dataset
uspto-grants-2015_07
Patent number
US09090583B2

Linked notes

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