4-Bromo-2-methylbut-1-ene → 2-Methoxy-1-[2,4,6-trihydroxy-3,5-di(3-methyl-2-buten-1-yl)phenyl]ethanone

HRID 1528034

Reaction equation

HRID 1528034 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:6]1[C:11]([OH:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]=1[OH:14])=[O:5].[CH2:15](Br)[CH2:16][C:17]([CH3:19])=[CH2:18]>[OH-].[K+]>[CH3:1][O:2][CH2:3][C:4]([C:6]1[C:7]([OH:14])=[C:8]([CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[C:9]([OH:13])=[C:10]([CH2:3][CH:4]=[C:6]([CH3:11])[CH3:7])[C:11]=1[OH:12])=[O:5]

Participants

4

Reactant 2

HCID 5495854-Bromo-2-methylbut-1-eneHCID 6434002-Methoxy-1-(2,4,6-trihydroxyphenyl)ethanone

Product 1

HCID 867022152-Methoxy-1-[2,4,6-trihydroxy-3,5-di(3-methyl-2-buten-1-yl)phenyl]ethanoneYield 41%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

2-methoxy-1-(2,4,6-trihydroxyphenyl)ethanone (8.3 g, 42 mmol) was dissolved in a 5% potassium hydroxide aqueous solution (84 ml). After the reaction mixture was cooled below 0° C., Isopentenyl bromide (12.48 g, 84 mmol) was slowly added dropwise to within 30 minutes. The reaction mixture was stirred at room temperature (RT) 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, followed by removing solvent. The desired compound was obtained by purifying the residue by silica gel column chromatography (dichloromethane as eluent) (5.7 g, yield 41%). 1H NMR (400 MHz, DMSO-d6): δ=11.44 (s, 2H), 9.24 (s, 1H), 5.00 (t, 2H, J=6.8 Hz), 4.63 (s, 2H,), 3.31 (s, 3H), 3.22 (d, 4H, J=6.8 Hz), 1.67 (s, 6H), 1.58 (s, 6H).

Workup

  1. temperatureAfter the reaction 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. customby removing solvent

Sources & evidence

ORD record
ord-53f269416ed1433b81d3fd78cfd8b932
Source dataset
uspto-grants-2015_07
Patent number
US09090583B2

Linked notes

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