Cyclohexanone, 2-[(4-methoxyphenyl)methylene]- → 2-(4-Methoxybenzyl)phenol

HRID 1158272

반응식

HRID 1158272 반응식
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH:7]=[C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[CH:5][CH:4]=1.C(OCC)(=O)/C=C\C(OCC)=O>[C].[Pd].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 364010Cyclohexanone, 2-[(4-methoxyphenyl)methylene]-HCID 5271566Diethyl Maleate

생성물 1

HCID 2584512-(4-Methoxybenzyl)phenol수율 62.1%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
180 °C

실험 절차

In a 100-ml, four-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer were placed 21.6 g (0.1 mole) of the 2-(4-methoxybenzylidene)cyclohexanone produced in Example 8 and 51.7 g (0.3 mole) of diethyl maleate in this order. The flask inside was purged with nitrogen. Thereto was added 2.2 g (10 wt. %, 1.0 mmole as palladium) of 5% palladium carbon (a product of Wako Pure Chemical Industries, Ltd.). The mixture was stirred at 180° C. for 6 hours and cooled to room temperature. 200 ml of toluene was added to the system. Filtration was conducted to remove the palladium carbon. The filtrate was extracted with 150 ml of a 7% aqueous sodium hydroxide solution, and this operation was repeated twice. The aqueous layer was washed with 50 ml of toluene. To the resulting aqueous layer was added 35% hydrochloric acid until the aqueous layer became acidic, after which the aqueous layer was extracted with 150 ml of ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous sodium chloride solution in this order. The ethyl acetate layer was dried over anhydrous sodium sulfate and then subjected to vacuum distillation to remove ethyl acetate, to obtain 13.3 g of light yellow crystals. Yield: 62% The purity of the intended product in the crystals was 97% as measured by high performance liquid chromatography.

후처리

  1. customIn a 100-ml, four-necked flask equipped with a mechanical stirrer, a reflux condenser
  2. customThe flask inside was purged with nitrogen
  3. temperaturecooled to room temperature
  4. filtrationFiltration
  5. customto remove the palladium carbon
  6. extractionThe filtrate was extracted with 150 ml of a 7% aqueous sodium hydroxide solution
  7. washThe aqueous layer was washed with 50 ml of toluene
  8. additionTo the resulting aqueous layer was added 35% hydrochloric acid until the aqueous layer
  9. extractionafter which the aqueous layer was extracted with 150 ml of ethyl acetate
  10. washThe ethyl acetate layer was washed with water
  11. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  12. distillationsubjected to vacuum distillation
  13. customto remove ethyl acetate

출처 및 근거

ORD 기록
ord-a1b916a1160f4df6b786e50dd1436849
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807856B2

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