Hydrochloric Acid → alpha-Tocopherol

HRID 376501

반응식

HRID 376501 반응식
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[CH:5][C:3]=1O.Cl.[CH3:13][CH:14]([CH2:16][CH2:17][CH2:18][CH:19]([CH2:21][CH2:22][CH2:23][CH:24]([CH2:26][CH2:27][CH2:28][C:29]([OH:33])([CH:31]=[CH2:32])[CH3:30])[CH3:25])[CH3:20])[CH3:15]>[Cl-].[Zn+2].[Cl-].C(OCC(C)C)(=O)C>[CH3:9][C:8]1[C:7]([OH:10])=[C:6]([CH3:11])[C:5]2[CH2:32][CH2:31][C@:29]([CH2:28][CH2:27][CH2:26][C@@H:24]([CH2:23][CH2:22][CH2:21][C@@H:19]([CH2:18][CH2:17][CH2:16][CH:14]([CH3:13])[CH3:15])[CH3:20])[CH3:25])([CH3:30])[O:33][C:3]=2[C:2]=1[CH3:1]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 10453IsophytolHCID 12785Trimethylhydroquinone

생성물 1

HCID 14985alpha-Tocopherol수율 102.2%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8038Isobutyl Acetate용매

반응 조건

온도
35 °C

실험 절차

To a mixture consisting of 69.9 g (0.460 mol) of 2,3,5-trimethylhydroquinone, 52.5 g (0.386 mol) of zinc chloride, 150 ml of isobutyl acetate and 7.5 g of concentrated hydrochloric acid, 138.3 g (0.459 mol) of isophytol (purity: 98.3%) was added dropwise under stirring at 30-40° C. over 3 hours. At the same temperature, the reaction mixture was stirred for an additional 2 hours. After the reaction mixture was washed with 30 ml of water, the solvent was distilled off. Toluene (300 ml) was added to the residue to dissolve the same. The resulting solution was washed successively with water, alkaline water and a saturated aqueous solution of NaCl, dried over magnesium sulfate and then concentrated under reduced pressure, whereby 202.0 g of the title compound was obtained as a brown oil (yield 99.6%, GLC purity: 97.5).

후처리

  1. additionwas added dropwise
  2. stirringAt the same temperature, the reaction mixture was stirred for an additional 2 hours
  3. washAfter the reaction mixture was washed with 30 ml of water
  4. distillationthe solvent was distilled off
  5. additionToluene (300 ml) was added to the residue
  6. dissolutionto dissolve the same
  7. washThe resulting solution was washed successively with water
  8. dry with materialalkaline water and a saturated aqueous solution of NaCl, dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5fe197cbf00d42d2bf19274f6e311a6a
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020505

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