Hydrochloric Acid → alpha-Tocopherol

HRID 376500

反応式

HRID 376500 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.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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 10453IsophytolHCID 12785Trimethylhydroquinone

生成物 1

HCID 14985alpha-Tocopherol収率 101.7%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8038Isobutyl Acetate溶媒

反応条件

温度
35 °C

実験手順

To a mixture consisting of 23.3 g (0.153 mol) of 2,3,5-trimethylhydroquinone, 17.5 g (0.128 mol) of zinc chloride, 50 ml of isobutyl acetate and 2.5 g of concentrated hydrochloric acid, 46.1 g (0.153 mol) of isophytol (purity: 98.3%) were 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 10 ml of water, the solvent was distilled off. Toluene (100 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 67.0 g of the title compound was obtained as a brown oil (yield: 98.6%, GLC purity: 98.6%, α-tocopheryl acetate content: 0.2%, isobutyl acetate recovery rate: 92%).

後処理

  1. additionwere 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 10 ml of water
  4. distillationthe solvent was distilled off
  5. additionToluene (100 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

出典と根拠

ORDレコード
ord-69dc75d9d2264d08a85d9aeba632d2f1
出典データセット
uspto-grants-2000_02
特許番号
US06020505

関連ノート

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