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HCID 14854590, 화합물 → (1-Cyanocyclohexyl)acetic acid

HRID 974434
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HRID 974434 반응식
[C:1]([C:3]1([CH:9](C(O)=O)[C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]>C1(C)C=CC=CC=1>[C:1]([C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]
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참가 물질

3

반응물 1

HCID 14854590HCID 14854590, 화합물

생성물 1

HCID 11073797(1-Cyanocyclohexyl)acetic acid수율 69.7%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
82.5 °C

실험 절차

35.5 g (1-Cyanocyclohexyl)-malonic acid are suspended in 400 mL toluene and heated, while stirring, for about one hour to 80-85° C. In the course of the decarboxylation, an almost clear solution is obtained. After filtration, the toluene is distilled off in a vacuum at 35° C. The crude product is dissolved in a saturated aqueous solution of sodium bicarbonate and stirred with ethyl acetate. After separating off the organic phase, the aqueous phase is acidified with concentrated hydrochloric acid, while cooling with ice to 5° C. The solid product which precipitates out is filtered off with suction and then washed with water. The filter cake is dissolved in ethyl acetate and the solution dried over anhydrous sodium sulphate. After filtration, the ethyl acetate is evaporated on a rotary evaporator at 35° C. The residue is dried to constant weight in a vacuum drying cabinet at 35° C. 19.6 g of the title compound are obtained (70% of theory); m.p. 102° C.

후처리

  1. temperatureheated
  2. customIn the course of the decarboxylation, an almost clear solution is obtained
  3. filtrationAfter filtration
  4. distillationthe toluene is distilled off in a vacuum at 35° C
  5. dissolutionThe crude product is dissolved in a saturated aqueous solution of sodium bicarbonate
  6. stirringstirred with ethyl acetate
  7. customAfter separating off the organic phase
  8. temperaturewhile cooling with ice to 5° C
  9. customThe solid product which precipitates out
  10. filtrationis filtered off with suction
  11. washwashed with water
  12. dissolutionThe filter cake is dissolved in ethyl acetate
  13. dry with materialthe solution dried over anhydrous sodium sulphate
  14. filtrationAfter filtration
  15. customthe ethyl acetate is evaporated on a rotary evaporator at 35° C
  16. customThe residue is dried to constant weight in a vacuum
  17. customdrying cabinet at 35° C

출처 및 근거

ORD 기록
ord-dfa11f63857848ae9c3d9245446b1ee6
출처 데이터셋
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05068413

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