Hydrogen Bromide → DL-alpha-Tocopherol

HRID 376506

반응식

HRID 376506 반응식
[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]

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 7766Diethyl CarbonateHCID 10453IsophytolHCID 12785Trimethylhydroquinone

생성물 1

HCID 2116DL-alpha-Tocopherol수율 101.2%

시약·촉매·용매 1

HCID 10421208Zinc bromide촉매

반응 조건

온도
50 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6e997ba4f955466e8f03b9847f05127f
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020505

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