Toluene → Ethyl alpha-hydroxyimino(5,6-dihydro-1,4-oxathiin-2-yl)acetate

HRID 437136ノート

反応式

HRID 437136 の反応式
O[CH2:2][CH2:3][S:4][CH2:5][C:6](=[O:15])[C:7](=[N:13][OH:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[OH:14][N:13]=[C:7]([C:6]1[O:15][CH2:2][CH2:3][S:4][CH:5]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

5

反応物 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 178472918HCID 178472918、化合物

生成物 1

HCID 86734852Ethyl alpha-hydroxyimino(5,6-dihydro-1,4-oxathiin-2-yl)acetate収率 92.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Ethyl 4-(2-hydroxy-ethylthio)-2-hydroxyimino-3-oxobutyrate (321 g.) is dissolved in boiling toluene (3.2 liters) and para-toluenesulphonic acid monohydrate (26 g.) is then added. Vigorous boiling occurs, with liberation of water, which is removed in a Dean-Stark apparatus. The heating of the reaction mixture is continued for 15 minutes. After cooling, the toluene solution is filtered and washed three times with water (a total of 1.5 liters), then with a saturated sodium bicarbonate solution (200 cc.) and finally with water (500 cc.). It is dried over magnesium sulphate, treated with decolourising charcoal, filtered and concentrated to dryness under reduced pressure (20 mm Hg). Ethyl α-hydroxyimino(5,6-dihydro-1,4-oxathiin-2-yl)acetate (273 g.) is obtained in the form of an oil which slowly solidifies.

後処理

  1. additionis then added
  2. customis removed in a Dean-Stark apparatus
  3. temperatureThe heating of the reaction mixture
  4. temperatureAfter cooling
  5. filtrationthe toluene solution is filtered
  6. washwashed three times with water (a total of 1.5 liters), then with a saturated sodium bicarbonate solution (200 cc.)
  7. dry with materialIt is dried over magnesium sulphate
  8. additiontreated with decolourising charcoal
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)

出典と根拠

ORDレコード
ord-5402cf626d1e4dc192394da4e2e0f9b5
出典データセット
uspto-grants-1977_06
特許番号
US04029781

反応ノート

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