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Sodium Chloride → trans-3,3-Dimethyl-2-acetyl-cyclopropanecarbaldehyde

HRID 2198515
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HRID 2198515 반응식
C(O)(C)(C)C.[Li].[CH3:7][C:8]1([CH3:17])[C@@H:10]([C:11](Cl)=[O:12])[C@@H:9]1[C:14](=[O:16])[CH3:15].[Cl-].[Na+]>O1CCCC1>[CH3:7][C:8]1([CH3:17])[C@@H:10]([CH:11]=[O:12])[C@@H:9]1[C:14](=[O:16])[CH3:15]
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참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 6386tert-ButanolHCID 3028194LithiumHCID 54262972trans-3,3-Dimethyl-2-acetyl-cyclopropanecarboxylic acid chloride

생성물 1

HCID 53675424trans-3,3-Dimethyl-2-acetyl-cyclopropanecarbaldehyde수율 62%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

36.6 g (0.495 mol) of tert.-butanol were added dropwise to a mixture of 6.3 g (0.165 mol) of lithium alanate and 100 ml of tetrahydrofuran at 20°-30° C. in the course of 1 hour. The mixture was subsequently stirred at room temperature for 2 hours and was then added dropwise to a solution of 26.1 g (0.15 mol) of trans-3,3-dimethyl-2-acetyl-cyclopropane-carboxylic acid chloride in 75 ml of tetrahydrofuran at -50° to -60° C. When the addition has ended, the mixture was subsequently stirred for 1 hour, without cooling, poured onto a mixture of 30 ml of concentrated sodium chloride and 300 g of ice and extracted twice by shaking with 400 ml of ether each time. The organic phases were first washed with 50 ml of saturated sodium bicarbonate solution and then with 100 ml of water, dried over sodium sulphate and evaporated in vacuo. Distillation of the residue in vacuo gave 12.7 g (62% of theory) of trans-3,3-dimethyl-2-acetyl-cyclopropane-carbaldehyde in the form of a colorless oil with a boiling point of 80°-86° C./10 mbars.

후처리

  1. additionWhen the addition
  2. stirringthe mixture was subsequently stirred for 1 hour
  3. temperaturewithout cooling
  4. extractionextracted twice
  5. stirringby shaking with 400 ml of ether each time
  6. washThe organic phases were first washed with 50 ml of saturated sodium bicarbonate solution
  7. dry with materialwith 100 ml of water, dried over sodium sulphate
  8. customevaporated in vacuo
  9. distillationDistillation of the residue in vacuo

출처 및 근거

ORD 기록
ord-d82bce10c0194e91b2d353859c9b0c0b
출처 데이터셋
uspto-grants-1982_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04358409

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