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Benzyl Bromide → Bis-(4-Benzyloxyphenyl)methanone

HRID 19959
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HRID 19959 반응식
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.O>[CH2:21]([O:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:6][C:5]3[CH:15]=[CH:16][CH:2]=[CH:3][CH:4]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 691504,4'-DihydroxybenzophenoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 10668342Bis-(4-Benzyloxyphenyl)methanone수율 193.7%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

To a solution of 4,4′-dihydroxybenzophenone (5.0 g, 23.34 mmol) in anhydrous DMF (150 mL) at 0° C. was added sodium hydride (60% in mineral oil, 2.1 g, 51.35 mmol), in two portions. After stirring for 20 min at which no more evolution of hydrogen was observed, benzyl bromide (8.96 g, 51.35 mmol) was added. The resulting yellow suspension was then stirred under an atmosphere of nitrogen at 100° C. for 1 h. Upon cooling to room temperature, water (500 mL) was added to the suspension and the precipitate that formed was filtered and washed exhaustively with water. After air-drying overnight at room temperature, the white solid (10.1 g) that collected was recrystallised from hot toluene to give LWO02007A as white flaky plate crystals (8.92 g, 22.61 mmol, 96.9%); m.p. 188-190° C.

후처리

  1. temperatureUpon cooling to room temperature
  2. customthe precipitate that formed
  3. filtrationwas filtered
  4. washwashed exhaustively with water
  5. customAfter air-drying overnight at room temperature
  6. customthe white solid (10.1 g) that collected
  7. customwas recrystallised from hot toluene

출처 및 근거

ORD 기록
ord-484c945682d749ad8dbb19cbbb404890
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745472B2

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