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Acetic Acid → HCID 12766830, 화합물

HRID 1577678
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HRID 1577678 반응식
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][C:5]=1[CH:6]=O)[CH3:2].[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][C:5]=1[CH:6]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15]([O:23][CH2:24][CH3:25])=[O:22])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 34343142,5-Diethoxybenzaldehyde

생성물 1

HCID 12766830HCID 12766830, 화합물수율 92%

시약·촉매·용매 2

HCID 241Benzene용매
HCID 962
Water
용매
2회

실험 절차

2,5-Diethoxybenzaldehyde (24 g., 0.124 mole) and diethyl malonate (20 g., 0.125 mole) are added to a solution of piperidine (3.0 g.) and glacial acetic acid (6 ml.) in benzene (160 ml.). The mixture is heated under reflux utilizing a Dean-Stark water separater until water ceased to be separated. After 8 hours of distillation 2.3 ml. of water out of a theoretical yield of 2.23 ml. are obtained and the reaction mixture cooled. The cooled reaction mixture is washed with aqueous hydrochloric acid (6 N, 70 ml.) water (70 ml.) and aqueous sodium bicarbonate (5% w/w, 50 ml.). The organic layer is separated, dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure to yield a yellow oil (42.7 g., 0.127 mole, 100%). Trituration with petroleum ether yields diethyl 2,5-Diethoxybenzylidenemalonate (38.4 g., 0.114 mole, 92%) m.p. (from petroleum ether) 52°-53° C. I.R.: 1720 cm- 1 mass spec m/e 336.

후처리

  1. temperatureThe mixture is heated
  2. temperatureunder reflux
  3. customto be separated
  4. distillationAfter 8 hours of distillation 2.3 ml
  5. customare obtained
  6. temperaturethe reaction mixture cooled
  7. customThe cooled reaction mixture
  8. washis washed with aqueous hydrochloric acid (6 N, 70 ml.) water (70 ml.) and aqueous sodium bicarbonate (5% w/w, 50 ml.)
  9. customThe organic layer is separated
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure
  13. customto yield a yellow oil (42.7 g., 0.127 mole, 100%)

출처 및 근거

ORD 기록
ord-411643c350b9497c836c5f31ae94a8c0
출처 데이터셋
uspto-grants-1981_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04288608

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