Hydrochloric Acid → 1,5-Bis(4-trifluoromethylphenyl)-penta-1,4-diene-3-one

HRID 1248066노트

반응식

HRID 1248066 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[OH-:13].[Na+].[Cl-].OCC[NH+](CCO)CCCCCCCC/C=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].Cl>CCCCCCC.C(O)(C)C.CC(C)=O.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:38][C:37](=[O:13])[CH:36]=[CH:35][C:34]2[CH:29]=[CH:30][C:31]([C:2]([F:12])([F:11])[F:1])=[CH:32][CH:33]=2)=[CH:5][CH:4]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 679964-(Trifluoromethyl)benzaldehydeHCID 86740137HCID 86740137, 화합물

생성물 1

HCID 5922411,5-Bis(4-trifluoromethylphenyl)-penta-1,4-diene-3-one수율 99.6%

시약·촉매·용매 4

HCID 180Acetone용매HCID 962Water용매HCID 3776Isopropanol용매HCID 8900Heptane용매2회

반응 조건

온도
40 °C

실험 절차

A mixture of 4-trifluoromethylbenzaldehyde (65.2 g; 0.369 mol), heptane (70 ml), 10% sodium hydroxide solution (15 g) and water (30 ml) is stirred under a nitrogen atmosphere and heated to 40° C. Next, a solution of acetone (10.7 g) and of bis(2-hydroxyethyl)methyloleylammonium chloride (1.6 g) in heptane (30 ml) is added dropwise over three hours at the above temperature. After the addition is completed, the mixture is stirred at 40° C. to 45° C. for two hours. After two hours, isopropyl alcohol (68 ml) and hydrochloric acid (9.4 ml; concentrated) are added and the mixture heated at reflux for 1.5 hours. The reaction mixture is then cooled to 20° C., the precipitated solid is isolated by filtration, washed with heptane (40 ml) and water to afford 56.8 g of 99.6% pure title product, mp 154° C. to 156° C. (83.0% yield).

후처리

  1. additionAfter the addition
  2. stirringthe mixture is stirred at 40° C. to 45° C. for two hours
  3. temperaturethe mixture heated
  4. temperatureat reflux for 1.5 hours
  5. temperatureThe reaction mixture is then cooled to 20° C.
  6. customthe precipitated solid is isolated by filtration
  7. washwashed with heptane (40 ml) and water

출처 및 근거

ORD 기록
ord-d9a2563ecb8642de8499abd3e7420b05
출처 데이터셋
uspto-grants-1985_06
특허 번호
US04521629

반응 노트

불러오는 중…