3-Methyl-2-buten-1-OL → HCID 53836050, compound

HRID 567211Notes

Reaction equation

HRID 567211 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]=1[OH:14])=[O:5].[CH3:16][C:17]([CH3:21])=[CH:18][CH2:19]O>O1CCOCC1>[CH3:16][C:17]([CH3:21])=[CH:18][CH2:19][C:8]1[C:7]([OH:14])=[C:6]([C:4]([CH2:3][CH:2]([CH3:15])[CH3:1])=[O:5])[C:11]([CH3:12])=[C:10]([CH2:9][CH:10]=[C:11]([CH3:12])[CH3:6])[C:9]=1[O:13][CH2:4][CH:3]=[C:2]([CH3:15])[CH3:1].[OH:14][C:7]1[C:8]([CH2:19][CH:18]=[C:17]([CH3:21])[CH3:16])=[C:9]([OH:13])[CH:10]=[C:11]([CH3:12])[C:6]=1[C:4]([CH2:3][CH:2]([CH3:15])[CH3:1])=[O:5]

Participants

5

Reactant 2

HCID 111733-Methyl-2-buten-1-OLHCID 54109422HCID 54109422, compound

Product 2

HCID 53836050HCID 53836050, compoundHCID 53921689HCID 53921689, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

To a solution of 1.04 g (5.00 mmol) of (2,4-dihydroxy-6-methylphenyl) (2-methylpropyl) ketone (47) in dry 1,4-dioxane (10.0 ml), under nitrogen atmosphere, added 710 mg (5.00 mmol, 1.00 equivalent) of boron trifluoride ether complex in dioxane (5.0 ml) at 10° C. with stirring. Then, added 861 mg (10.0 mmol, 2.00 equivalents) of 3-methyl-2-butenol in dioxane (5.0 ml) slowly, allowing to elevate to room temperature, and stirred for five hours. Added ether to the reaction mixture and washed the ether layer with saturated sodium hydrogen carbonate aqueous solution and saturated brine, and dried over sodium sulfate. By removal of the solvent, obtained orange-colored oily substance as a crude product. Column chromatographic separation on silica gel (65 g of Wako Gel C-300, eluted with hexane: ethyl acetate at varying ratios=19:1-7:3) gave, in the order of elution, 246 mg of {3,5-bis(3-methyl-2-butenyl)-2-hydroxy-6-methyl-4-(3-methyl-2-butenyloxy)phenyl}(2-methylpropyl) ketone (51) as a light yellow viscous oil and 95 mg of {2,4-dihydroxy-6-methyl-3-(3-methyl-2-butenyl)phenyl}(2-methylpropyl) ketone (49) as a light yellow fine needles.

Workup

  1. customto elevate to room temperature
  2. stirringstirred for five hours
  3. washAdded ether to the reaction mixture and washed the ether layer with saturated sodium hydrogen carbonate aqueous solution and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customBy removal of the solvent
  6. customobtained orange-colored oily substance as a crude product
  7. customColumn chromatographic separation on silica gel (65 g of Wako Gel C-300, eluted with hexane: ethyl acetate at varying ratios=19:1-7:3)

Sources & evidence

ORD record
ord-ac1e45c353ec476bb4aca9f1fe60a5e9
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

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