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

HRID 6319Notes

Reaction equation

HRID 6319 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 of 3 ml of water and 10 ml of n-butanol. After conclusion of the dropping, the 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 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. extractionthe reaction solution was extracted with ether
  4. customthe extracted solution was dried
  5. concentrationconcentrated
  6. customThe concentrate was purified by column chromatography
  7. customto obtain 4.8 g of the objective ether compound

Sources & evidence

ORD record
ord-b4667a9cf3b446bd948f6814dceebf7a
Source dataset
uspto-grants-1993_09
Patent number
US05248446

Reaction notes

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