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

HRID 1612586

Reaction equation

HRID 1612586 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-toluenesufonate 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

Sources & evidence

ORD record
ord-207c851bb48e4a778e62958d6f46b8d8
Source dataset
uspto-grants-1993_03
Patent number
US05190686

Linked notes

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