Hydroquinone → Phenol, 4-(2-methylbutoxy)-

HRID 6313

Reaction equation

HRID 6313 reaction equation
[C:1]1([CH3:16])[CH:6]=CC(S(OCC(C)CC)(=O)=O)=[CH:3][CH:2]=1.[C:17]1([CH:24]=[CH:23][C:21]([OH:22])=[CH:20][CH:19]=1)[OH:18].[OH-].[Na+]>O.C(O)CCC>[CH3:6][CH:1]([CH2:2][CH3:3])[CH2:16][O:18][C:17]1[CH:24]=[CH:23][C:21]([OH:22])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 14798Sodium HydroxideHCID 3011991-Butanol, 2-methyl-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 106720Phenol, 4-(2-methylbutoxy)-Yield 72%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

Into a n-butanol suspension containing 37 mmol (9.0 g) of 2-methylbutyl p-toluenesulfonate prepared by tosylating S-(-)-2-methylbutanol and 74 mmol (8.2 g) of hydroquinone, added dropwise was a solution of 50 mmol (2.1 g) of sodium hydroxide dissolved in a solvent mixture comprising 3 ml of water and 10 ml of n-butanol, and the obtained mixture was then stirred for 8 hours at 120° C. After addition of water, the reaction solution was extracted with ether, and the extracted solution was dried and concentrated. The resulting concentrate was purified by column chromatography to obtain 4.8 g of the objective ether compound (Yield: 72%).

Workup

  1. customprepared
  2. additionadded dropwise
  3. dissolutiondissolved in a solvent mixture
  4. extractionthe reaction solution was extracted with ether
  5. customthe extracted solution was dried
  6. concentrationconcentrated
  7. concentrationThe resulting concentrate
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ee68d39c5e5542ca8e4b4663ce20dbb7
Source dataset
uspto-grants-1993_09
Patent number
US05248446

Linked notes

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