Ethylene Glycol → Benzyl oximino-acetoacetate ethylene ketal

HRID 426890ノート

反応式

HRID 426890 の反応式
O.[N:2](=[CH:4][C:5](=[O:17])[CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[OH:3].[CH2:18](O)[CH2:19][OH:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:19]1[O:20][C:5]([CH:4]=[N:2][OH:3])([CH2:6][C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[O:17][CH2:18]1

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 86734531HCID 86734531、化合物

生成物 1

HCID 86734545Benzyl oximino-acetoacetate ethylene ketal収率 94%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

In a two liter flask fitted with a Dean Stark water separator and a condenser were placed in 186.5 g. (0.85 mole) of benzyl oximino-acetoacetate [1.1], 62 g. (1 mole) of ethylene glycol, 800 ml. of benzene (reagent grade) and 2 g. (10.5 mmole) of p-toluenesulfonic acid monohydrate. The reaction mixture was boiled at reflux until 15 ml. of water was removed (3 hours). The benzene solution was washed once with saturated sodium bicarbonate solution and once with brine. After drying over anhydrous sodium sulfate, the benzene solution was evaporated, leaving 212 g. (94% yield) of benzyl oximino-acetoacetate ethylene ketal [2.1] as a light yellow oil! Its NMR spectrum was consistent with the assigned structure. Generally, the product was used as such in subsequent reactions but one of the isomers can be crystallized2 from toluene-petroleum either (b.p. 30°-60° C.); m.p. 52° C.

後処理

  1. temperatureat reflux until 15 ml
  2. customof water was removed (3 hours)
  3. washThe benzene solution was washed once with saturated sodium bicarbonate solution and once with brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe benzene solution was evaporated
  6. customleaving 212 g

出典と根拠

ORDレコード
ord-fc1ea6eaeda34dd2b4bf2b73d7ec0e38
出典データセット
uspto-grants-1979_10
特許番号
US04171438

反応ノート

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