Mesityl oxide → Ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate

HRID 3979

반응식

HRID 3979 반응식
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[O:10]=[C:11]([CH:13]=[C:14]([CH3:16])[CH3:15])C.[CH3:17]CCCCCC>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[O:10]=[C:11]1[CH2:13][C:14]([CH3:16])([CH3:15])[CH:2]([C:1]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([CH3:17])=[CH:5]1

참가 물질

6

반응물 3

HCID 8858Mesityl oxideHCID 8868Ethyl AcetoacetateHCID 8900Heptane

생성물 1

HCID 90877Ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate수율 27%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 1140Toluene용매

실험 절차

A mixture of 1020 ml (1041 g, 8.00 mol) of ethyl acetoacetate, 960 ml (824 g, 8.40 mol) of mesityl oxide, 1000 ml of heptane, 600 ml of toluene, and 175 g of zinc chloride was heated at reflux in a 5000 ml round bottom flask while stirring. The flask was equipped with a Dean-Stark trap and drying tube. After 24 h, an additional 25 g of zinc chloride was added and refluxing continued for 36 h. After cooling, the reaction mixture was washed with 1500 ml of water, 5% sodium bicarbonate solution (2×1000 ml), and another 1500 ml of water. Removal of solvent by evaporation yielded 979 g of crude product. Distillation of the crude product provided 453.5 g of the desired ester which represents 27.0% yield. Distillation was at 124°-5° C. (3.0 torr).

후처리

  1. temperaturewas heated
  2. temperatureat reflux in a 5000 ml round bottom flask
  3. customThe flask was equipped with a Dean-Stark trap
  4. customdrying tube
  5. additionan additional 25 g of zinc chloride was added
  6. temperaturerefluxing
  7. waitcontinued for 36 h
  8. temperatureAfter cooling
  9. washthe reaction mixture was washed with 1500 ml of water, 5% sodium bicarbonate solution (2×1000 ml)
  10. customRemoval of solvent
  11. customby evaporation
  12. customyielded 979 g of crude product
  13. distillationDistillation of the crude product

출처 및 근거

ORD 기록
ord-e48263ea1c184915ac82de02fc1d25d1
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723038

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