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

HRID 2102979

반응식

HRID 2102979 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 692112,5-Dimethylhydroquinone

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-043b5855919c432a848375f174ac4422
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576094B2

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