Hydrogen Bromide → DL-alpha-Tocopherol

HRID 376506

反応式

HRID 376506 の反応式
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1O.C(=O)(OCC)OCC.Br.[CH3:21][CH:22]([CH2:24][CH2:25][CH2:26][CH:27]([CH2:29][CH2:30][CH2:31][CH:32]([CH2:34][CH2:35][CH2:36][C:37]([OH:41])([CH:39]=[CH2:40])[CH3:38])[CH3:33])[CH3:28])[CH3:23]>[Br-].[Zn+2].[Br-]>[CH3:9][C:8]1[C:2]([CH3:1])=[C:3]2[C:5]([CH2:40][CH2:39][C:37]([CH2:36][CH2:35][CH2:34][CH:32]([CH2:31][CH2:30][CH2:29][CH:27]([CH2:26][CH2:25][CH2:24][CH:22]([CH3:21])[CH3:23])[CH3:28])[CH3:33])([CH3:38])[O:41]2)=[C:6]([CH3:11])[C:7]=1[OH:10]

参加物

6

反応物 4

HCID 260Hydrogen BromideHCID 7766Diethyl CarbonateHCID 10453IsophytolHCID 12785Trimethylhydroquinone

生成物 1

HCID 2116DL-alpha-Tocopherol収率 101.2%

試薬・触媒・溶媒 1

HCID 10421208Zinc bromide触媒

反応条件

温度
50 °C

実験手順

To a mixture consisting of 23.3 g (0.153 mol) of 2,3,5-trimethylhydroquinone, 23.2 g (0.153 mol) of zinc bromide, 52.9 ml of diethyl carbonate and 4.3 g of 47% hydrobromic acid, was added dropwise, under stirring at 50±5° C. over one hour, 46.2 g (0.153 ml) of isophytol (purity: 98.1%). Further, the resulting mixture was stirred for one hour at the same temperature. The reaction liquid was washed several times with 50 ml of water, followed by concentrating under a reduced pressure, whereby 66.7 g of the title compound was obtained as a brown oil (yield: 99.1 %, GLC purity: 98.0%).

後処理

  1. additionwas added dropwise
  2. stirringFurther, the resulting mixture was stirred for one hour at the same temperature
  3. customThe reaction liquid
  4. washwas washed several times with 50 ml of water
  5. concentrationby concentrating under a reduced pressure

出典と根拠

ORDレコード
ord-6e997ba4f955466e8f03b9847f05127f
出典データセット
uspto-grants-2000_02
特許番号
US06020505

関連ノート

読み込み中…