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

HRID 1158271

반응식

HRID 1158271 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:11]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[OH-].[Na+]>CCCCCC.C1(C)C=CC=CC=1.O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:1]=[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:11]2=[O:17])=[CH:3][CH:4]=1

참가 물질

7

반응물 3

HCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

생성물 1

HCID 364010Cyclohexanone, 2-[(4-methoxyphenyl)methylene]-수율 74.3%

시약·촉매·용매 3

HCID 962Water용매3회HCID 1140Toluene용매2회HCID 8058Hexane용매

반응 조건

온도
65 °C

실험 절차

In a 1,000-ml, four-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer were placed 68 g (0.5 mole) of p-anisaldehyde, 147 g (1.5 moles) of cyclohexanone and then 200 ml of water slowly. Thereto was slowly added, in a water bath, an aqueous solution obtained by diluting 80 g (0.5 mole) of a 25% aqueous sodium hydroxide solution, with 300 ml of water. The system was stirred at 65° C. for 48 hours and cooled to room temperature. To the system were added 400 ml of toluene and 100 ml of water for phase separation. The aqueous layer was re-extracted with 100 ml of toluene. The toluene layers were combined and washed with water and a saturated aqueous sodium chloride solution in this order. The resulting toluene layer was dried over anhydrous sodium sulfate and subjected to vacuum distillation to remove toluene and the excessive (remaining) cyclohexanone. To the crude oil obtained were added 80 ml of toluene and 80 ml of n-hexane for recrystallization, to obtain 80.4 g of yellow crystals. Yield: 74% The purity of the intended product in the crystals was 88% as measured by high performance liquid chromatography.

후처리

  1. customIn a 1,000-ml, four-necked flask equipped with a mechanical stirrer, a reflux condenser
  2. additionThereto was slowly added, in a water bath
  3. customan aqueous solution obtained
  4. temperaturecooled to room temperature
  5. customfor phase separation
  6. extractionThe aqueous layer was re-extracted with 100 ml of toluene
  7. washwashed with water
  8. dry with materialThe resulting toluene layer was dried over anhydrous sodium sulfate
  9. distillationsubjected to vacuum distillation
  10. customto remove toluene
  11. customTo the crude oil obtained
  12. customfor recrystallization

출처 및 근거

ORD 기록
ord-1a100f660b95437fb00b7c94b235feda
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807856B2

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