Methanol → 1,3-Propanedione, 1,3-bis(4-bromophenyl)-

HRID 355616

반응식

HRID 355616 반응식
C[C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[H-].[Na+].[CH3:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)=[O:16].CO>C1C=CC=CC=1>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([C:15](=[O:16])[CH2:14][C:4](=[O:6])[C:3]2[CH:2]=[CH:10][C:9]([Br:11])=[CH:8][CH:7]=2)=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 7466p-BromoacetophenoneHCID 24758Sodium hydrideHCID 995704-Bromo-2-methylbenzoic acid

생성물 1

HCID 1474381,3-Propanedione, 1,3-bis(4-bromophenyl)-

시약·촉매·용매 1

HCID 241Benzene용매2회

반응 조건

온도
60 °C

실험 절차

In a 1-liter three neck round bottom flask , 43 g (0.2 mol) methyl 4-bromobenzoic acid and 17.6 g (0.4 mol) sodium hydride were dissolved in 200 ml dried benzene and heated to 60° C. Next, 39.8 g (0.2 mol) 4-bromoacetophenone in 100 ml dry benzene was slowly added through a dropping f umnel, and 1 ml methanol was added to the flask to initiate the reaction. After the mixture was refluxed overnight, the reaction was quenched by adding methanol and pouring it into ice water. The pH of the mixture was brought down to 7.0 using 5N sulfuric acid. A solid was collected, washed with water, and recrystallized from benzene to give a light yellow product. Characterization. Yield: 30.3 g (40%). 1H NMR (300 MHz, CDCl3, 20° C., δ): 7.84 (d, 4H, ArH); 7.62 (d, 4H, ArH); 6.77(s, 2H, CH2). EI-MS: 382(M+), 301, 225, 183, 157.

후처리

  1. additionwas added to the flask
  2. customthe reaction
  3. temperatureAfter the mixture was refluxed overnight
  4. customthe reaction was quenched
  5. additionby adding methanol
  6. additionpouring it into ice water
  7. customA solid was collected
  8. washwashed with water
  9. customrecrystallized from benzene
  10. customto give a light yellow product

출처 및 근거

ORD 기록
ord-caee3de8e69648dcbc763c5f24300194
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834100

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