2,5-Dimethyl-4-benzoquinone → 2,5-Dimethylhydroquinone

HRID 2102979Notes

Reaction equation

HRID 2102979 reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([CH3:9])[C:6](=[O:8])[CH:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[CH3:9][C:5]1[CH:4]=[C:3]([OH:10])[C:2]([CH3:1])=[CH:7][C:6]=1[OH:8]

Participants

4

Reactant 2

HCID 87182,5-Dimethyl-4-benzoquinoneHCID 24489Sodium Dithionite

Product 1

HCID 692112,5-Dimethylhydroquinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,5-Dimethylbenzoquinone (5 g) in ethyl acetate was shaken with an aqueous solution of sodium hydrosulfite. The organic layer was separated, washed, dried and evaporated to yield 2,5-dimethylhydroquinone. To a solution of 2,5-dimethylhydroquinone (5 g), prepared as described above, and 3-methyl-2-buten-1-ol (3.1 g) in dioxane (20 mL) was added BF3-ether (4.5 mL) at room temperature under nitrogen. The solution was stirred at room temperature for one hour, extracted with ethyl acetate, washed with water and dried. The mixture containing starting material and alkylated product was hydrogenated in methanol (100 mL) with 5 drops of concentrated HCl in the presence of Pd/C (10%, 200 mg) at60 psi for 18 hours. Workup and chromatography (silica gel hexane-ethyl acetate 5% to 12%) gave 2 g of the desired product, 2,5-dimethyl-3-(3-methyl-butyl)-hydroquinone.

Workup

  1. customThe organic layer was separated
  2. washwashed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-043b5855919c432a848375f174ac4422
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…