Acetone → 1,5-Bis(2-methylphenyl)-1,4-pentadien-3-one

HRID 714179노트

반응식

HRID 714179 반응식
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:10][C:11](=[O:12])[CH:13]=[CH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH3:4]

참가 물질

6

반응물 4

HCID 180AcetoneHCID 962WaterHCID 107222-MethylbenzaldehydeHCID 14798Sodium Hydroxide

생성물 1

HCID 45639421,5-Bis(2-methylphenyl)-1,4-pentadien-3-one수율 43.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-Methylbenzaldehyde (1ac, 1.45 ml, 12.5 mmol) and acetone (19, 0.46 ml, 6.3 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (2.61 g, 65.3 mmol) and water (25 ml) was added and the mixture stirred for 3 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethanol to give 0.71 g (43%) of a yellow solid: mp 98-100° C. [expected mp 94-96° C.]; 1H NMR: δ 2.47 (s, 6H), 6.98 (d, 2H, J=15.9 Hz), 7.24 (m, 6H), 7.64 (d, 2H, J=7.2 Hz), 8.03 (d, 2H, J=15.9 Hz); 13C NMR: δ 19.7, 126.1, 126.2, 126.5, 129.9, 130.7, 133.6, 137.9, 140.5, 188.5.

후처리

  1. stirringthe mixture stirred for 3 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-86a3e5959b704d6aba45fb3efda5f2b0
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187397B2

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