3-Methyl-2-buten-1-OL → HCID 86605473、化合物

HRID 2102980

反応式

HRID 2102980 の反応式
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[OH:4].[CH3:11][C:12]([CH3:16])=[CH:13][CH2:14]O>O1CCOCC1>[CH3:1][C:2]1[C:8]([CH2:14][CH2:13][CH:12]([CH3:16])[CH3:11])=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[OH:4]

参加物

4

反応物 2

HCID 111733-Methyl-2-buten-1-OLHCID 692112,5-Dimethylhydroquinone

生成物 1

HCID 86605473HCID 86605473、化合物収率 26.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane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. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. additionThe mixture containing
  5. waitwas 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

出典と根拠

ORDレコード
ord-e0423c6e2b61468f832782cdc85003c5
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…