4-Methylcatechol → 4-Methyl-5-phenylsulphonyl-1,2-benzenediol

HRID 745787

Reaction equation

HRID 745787 reaction equation
O.O.O.C([O-])(=O)C.[Na+].[Na].[C:10]1([S:16]([OH:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:19][C:20]1[CH:21]=[C:22]([OH:27])[C:23]([OH:26])=[CH:24][CH:25]=1>O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[Fe+3]>[CH3:19][C:20]1[CH:21]=[C:22]([OH:27])[C:23]([OH:26])=[CH:24][C:25]=1[S:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:18])=[O:17]

Participants

7

Reactant 4

HCID 99584-MethylcatecholHCID 12057Benzenesulfinic acidHCID 5360545SodiumHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 233120964-Methyl-5-phenylsulphonyl-1,2-benzenediol

Reagents, catalysts & solvents 2

HCID 26250Potassium ferricyanideCatalystHCID 962WaterSolvent2×

Procedure

A solution of 50 g (152 mmol) of potassium hexacyanoferrate (III) and 95 g of sodium acetate trihydrate in 200 ml of water is added dropwise in the course of 30 minutes, at room temperature under nitrogen, to a solution of 16.4 g (100 mmol) of the sodium salt of benzenesulphinic acid and 13.6 g (110 mmol) of 4-methyl-1,2-benzenediol in 150 ml of water. After stirring for 11/2 hours, the reaction mixture is acidified and repeatedly extracted with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution, dried over sodium sulphate and concentrated by evaporation. The residue is recrystallised from ether/hexane, yielding 4-methyl-5-phenylsulphonyl-1,2-benzenediol having a melting point of 145°-149°.

Workup

  1. extractionrepeatedly extracted with ethyl acetate
  2. washThe combined organic phases are washed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. customThe residue is recrystallised from ether/hexane

Sources & evidence

ORD record
ord-f8753f5ab7b34004afdf33dabddc38ba
Source dataset
uspto-grants-1986_07
Patent number
US04600709

Linked notes

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