Acetone → HCID 57878779, compound

HRID 1928687Notes

Reaction equation

HRID 1928687 reaction equation
C=CC[C:4]1[CH:9]=[C:8]([O:10][C:11]2[C:16]([OH:17])=[C:15]([OH:18])[CH:14]=[C:13]([CH2:19][CH:20]=[CH2:21])[CH:12]=2)[CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28]I.[CH3:30][C:31]([CH3:33])=O>C(OC(=O)C)C.CCCCCC>[CH2:30]([C:5]1[CH:4]=[CH:9][C:8]([O:10][C:11]2[C:16]([O:17][CH3:28])=[C:15]([OH:18])[CH:14]=[C:13]([CH2:19][CH:20]=[CH2:21])[CH:12]=2)=[CH:7][CH:6]=1)[CH:31]=[CH2:33]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 45270574HCID 45270574, compound

Product 1

HCID 57878779HCID 57878779, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of obovatol (1 g) in acetone (200 ml) were added potassium carbonate (K2CO3) (1.1 g) and methyl iodide (0.3 g), followed by stirring the solution at room temperature for 5 hours. After completion of the reaction, the organic layer containing the active material was collected and concentrated in a vacuum. The concentrate (1.2 g) was dissolved in methylene chloride (30 ml) and loaded onto a silica gel (Merck, Art No. 9385) so as to adsorb the active material thereonto. Silica gel column chromatography eluting with a gradient of a mixture of ethylacetate and hexane from 10:90 to 20:80 afforded colorless 3-(4-allylphenoxy)-5-allyl-2-methoxyphenol (0.91 g, yield 90%).

Workup

  1. customAfter completion of the reaction
  2. additionthe organic layer containing the active material
  3. customwas collected
  4. concentrationconcentrated in a vacuum
  5. concentrationThe concentrate (1.2 g)
  6. dissolutionwas dissolved in methylene chloride (30 ml)

Sources & evidence

ORD record
ord-6b2733b806304d3bb513ac60ed70d70e
Source dataset
uspto-grants-2012_05
Patent number
US08183405B2

Reaction notes

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