Hydroquinone → 4-[(Undec-10-en-1-yl)oxy]phenol

HRID 863362Notes

Reaction equation

HRID 863362 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])(=O)=O)=CC=1.[C:23]1([CH:30]=[CH:29][C:27]([OH:28])=[CH:26][CH:25]=1)[OH:24]>C(O)CCC.[Na].[Hg]>[CH2:21]([O:24][C:23]1[CH:30]=[CH:29][C:27]([OH:28])=[CH:26][CH:25]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]

Participants

5

Reactant 2

HCID 785HydroquinoneHCID 11141895HCID 11141895, compound

Product 1

HCID 183260014-[(Undec-10-en-1-yl)oxy]phenolYield 47.6%

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 2631-ButanolSolvent3×

Conditions

Temperature
110 °C

Procedure

2.60 g (8.02 mM) of 10-undecenyl p-toluenesulfonate and 1.79 g (16.2 mM) of hydroquinone were well mixed with 3 ml of butanol under stirring. Into the solution, a solution of 0.419 (9.74 mM) of sodium amalgam dissolved in 6 ml of butanol, followed by 7 hours of heat-refluxing at 110° C. After the reaction, butanol was distilled off, followed by addition of water and extraction with ether. To the ether extract liquid was added anhydrous sodium sulfate for drying, followed by distilling-off of ether and purification by column chromatography (developer solvent: methylene chloride) to obtain 1.00 g (3.82 mM) of p-(10-undecenyl)oxyphenol. Yield: 47.6%.

Workup

  1. distillationwas distilled off
  2. additionfollowed by addition of water and extraction with ether
  3. extractionTo the ether extract liquid
  4. additionwas added anhydrous sodium sulfate
  5. customfor drying
  6. distillationfollowed by distilling-off of ether and purification by column chromatography (developer solvent: methylene chloride)

Sources & evidence

ORD record
ord-36e3105f15c94d018cd22b164ea99112
Source dataset
uspto-grants-1998_02
Patent number
US05720898

Reaction notes

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