Benzyl Bromide → Bis-(4-Benzyloxyphenyl)methanone

HRID 19959

반응식

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 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 962Water용매HCID 6228Dimethylformamide용매

반응 조건

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
특허 번호
US07745472B2

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