Pyridine → Alpha-Tocopherol Acetate

HRID 443059

反応式

HRID 443059 の反応式
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[C:5]2[CH2:10][CH2:11][C@:12]([CH2:15][CH2:16][CH2:17][C@@H:18]([CH2:20][CH2:21][CH2:22][C@@H:23]([CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH3:24])[CH3:19])([CH3:14])[O:13][C:4]=2[C:3]=1[CH3:31].[C:32](OC(=O)C)(=[O:34])[CH3:33].N1C=CC=CC=1>CCCCCC>[CH3:31][C:3]1[C:4]2[O:13][C@@:12]([CH2:15][CH2:16][CH2:17][C@@H:18]([CH2:20][CH2:21][CH2:22][C@@H:23]([CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH3:24])[CH3:19])([CH3:14])[CH2:11][CH2:10][C:5]=2[C:6]([CH3:9])=[C:7]([O:8][C:32]([CH3:33])=[O:34])[C:2]=1[CH3:1]

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14985alpha-Tocopherol

生成物 1

HCID 86472Alpha-Tocopherol Acetate

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

The crude α-tocopherol is treated with 25.0 g of acetic anhydride (corresponding to 244.9 mmol), 25.0 g of pyridine (corresponding to 316.1 mmol) and 1.0 g of 4-dimethyl-aminopyridine (corresponding to 8.2 mmol; catalytic amount) and stirred for one hour at room temperature. The reaction mixture is poured on to 100 g of ice/water (about 1:1), stirred for 30 minutes, treated with 250 ml of n-hexane and washed in succession twice with 150 ml of water each time, twice with 100 ml of 2N sulphuric acid each time, with 150 ml of water, with 150 ml of saturated sodium bicarbonate solution and three times with 150 ml of water each time. Thereafter, the mixture is dried over 3 g of anhydrous magnesium sulphate for 10 minutes while stirring. After filtration, distillation of the solvent at 400 mbar and a bath temperature of 60° C. and subsequent drying for 30 minutes at 15 mbar and a bath temperature of 70° C. there are obtained 29.26 g of α-tocopherol acetate as a yellow oil, α-tocopherol acetate content (GC, internal standard squalane) 87.5%, chemical yield (α-tocopherol acetate) 93.1%. This crude acetate is distilled in a bulb tube oven (250° C./10-1 mbar). There are obtained 26.25 g of α-tocopherol acetate as a slightly yellowish oil which crystallizes slowly upon standing at room temperature. α-Tocopherol acetate content (GC, internal standard squalane) 96.2%, chemical yield 91.8%; stereo-chemical purity: 99.6% R,R,R-α isomer (HPLC of the methyl ether derivative on Chiracel OD, n-hexane); the product is identical with α-tocopheryl acetate according to 1H-NMR, IR, MS and microanalytical data.

後処理

  1. stirringstirred for 30 minutes
  2. washwashed in succession twice with 150 ml of water each time
  3. dry with materialThereafter, the mixture is dried over 3 g of anhydrous magnesium sulphate for 10 minutes
  4. stirringwhile stirring
  5. filtrationAfter filtration, distillation of the solvent at 400 mbar and a bath temperature of 60° C.
  6. customsubsequent drying for 30 minutes at 15 mbar and a bath temperature of 70° C.

出典と根拠

ORDレコード
ord-8740ac4e301241798da9bc019a5a1b17
出典データセット
uspto-grants-1999_04
特許番号
US05892058

関連ノート

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