Flopropione → 1-[2,4,6-Trihydroxy-3,5-di(3-methyl-2-buten-1-yl)phenyl]propan-1-one

HRID 1528039Notes

Reaction equation

HRID 1528039 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:13])[CH2:11][CH3:12].[CH2:14](Br)[CH2:15][C:16]([CH3:18])=[CH2:17]>[OH-].[K+]>[OH:1][C:2]1[C:7]([CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[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:13])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 3362FlopropioneHCID 5495854-Bromo-2-methylbut-1-ene

Product 1

HCID 867022171-[2,4,6-Trihydroxy-3,5-di(3-methyl-2-buten-1-yl)phenyl]propan-1-oneYield 36%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

1-(2,4,6-trihydroxyphenyl)propan-1-one (2.0 g, 11.0 mmol) was dissolved in a 5% potassium hydroxide aqueous solution (20 mL). After the mixture was cooled below 0° C., isopentenyl bromide (3.3 g, 22 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 solvent, The residue was purified by silica gel column chromatography (dichloromethane as eluent) to give the desired compound (0.63 g, yield 18%).

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 solvent
  6. customThe residue was purified by silica gel column chromatography (dichloromethane as eluent)

Sources & evidence

ORD record
ord-a0d291d28ccd481eb597b9abd063d710
Source dataset
uspto-grants-2015_07
Patent number
US09090583B2

Reaction notes

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