Water → 2,6-Di-tert-butylhydroquinone

HRID 23804

Reaction equation

HRID 23804 reaction equation
O.S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:10]([C:14]1[C:15](=[O:25])[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:18](=[O:20])[CH:19]=1)([CH3:13])([CH3:12])[CH3:11]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C>[C:10]([C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]=1[OH:25])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 962WaterHCID 128672,6-Di-t-butyl-p-benzoquinoneHCID 24489Sodium Dithionite

Product 1

HCID 755502,6-Di-tert-butylhydroquinone

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To 60 mL of water, 15.8 g (90.8 mmol) of sodium hydrosulfite, 50 mL of ethyl acetate, 10.0 g (45.5 mmol) of 2,6-di-tert-butyl-1,4-benzoquinone and 1.04 g (4.57 mmol) of benzyltriethylammonium chloride were added and the mixture was stirred for 1 hour at 25° C. The reaction mixture was subjected to liquid-liquid separation and the aqueous layer was discarded. The organic layer was washed with 20 mL of 10% aqueous sodium chloride and the solvent was distilled off under reduced pressure to give 2,6-di-tert-butylhydroquinone.

Workup

  1. customThe reaction mixture was subjected to liquid-liquid separation
  2. washThe organic layer was washed with 20 mL of 10% aqueous sodium chloride
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-af7933a982704aeda178c2934657f442
Source dataset
uspto-grants-2005_02
Patent number
US06852867B2

Linked notes

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