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

HRID 2102979

反応式

HRID 2102979 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 692112,5-Dimethylhydroquinone

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-043b5855919c432a848375f174ac4422
出典データセット
uspto-grants-2009_08
特許番号
US07576094B2

関連ノート

読み込み中…