Hydrochloric Acid → HCID 178444555, 화합물

HRID 1731460

반응식

HRID 1731460 반응식
[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]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 178444522HCID 178444522, 화합물

생성물 1

HCID 178444555HCID 178444555, 화합물수율 90%

반응 조건

온도
180 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-76b499c8b51949d4bec2154ee3285754
출처 데이터셋
uspto-grants-1986_11
특허 번호
US04621901

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