Hydrochloric Acid → HCID 178444555、化合物

HRID 1731460

反応式

HRID 1731460 の反応式
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H](C#N)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].[OH-:14].[K+].Cl.C(O)CO[CH2:20][CH2:21][OH:22]>>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:20]([C:21]([OH:22])=[O:14])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 178444522HCID 178444522、化合物

生成物 1

HCID 178444555HCID 178444555、化合物収率 90%

反応条件

温度
180 °C

実験手順

A solution of 2.9 g of trans-4-(4-pentenyl)cyclohexanecarbonitrile in 80 ml of diethylene glycol was treated with 8.0 g of potassium hydroxide and the mixture was stirred for 3.5 hours at a bath temperature of 180° C. Subsequently, the reaction mixture was treated with ice, made acid with 25 ml of 25% hydrochloric acid and partitioned in methylene chloride/water. The aqueous phase was extracted three times with methylene chloride. The organic phases were washed twice with water, dried over magnesium sulphate, filtered and concentrated. Chromatographic separation of the brown, oily residue (3.5 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 2.9 g (90%) of trans-4-(4-pentenyl)cyclohexanecarboxylic acid as a yellowish oil.

後処理

  1. additionSubsequently, the reaction mixture was treated with ice
  2. custompartitioned in methylene chloride/water
  3. extractionThe aqueous phase was extracted three times with methylene chloride
  4. washThe organic phases were washed twice with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customChromatographic separation of the brown, oily residue (3.5 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90)

出典と根拠

ORDレコード
ord-76b499c8b51949d4bec2154ee3285754
出典データセット
uspto-grants-1986_11
特許番号
US04621901

関連ノート

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