Benzyl Bromide → Bis-(4-Benzyloxyphenyl)methanone

HRID 19959

反応式

HRID 19959 の反応式
[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

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 691504,4'-DihydroxybenzophenoneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 10668342Bis-(4-Benzyloxyphenyl)methanone収率 193.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-484c945682d749ad8dbb19cbbb404890
出典データセット
uspto-grants-2010_06
特許番号
US07745472B2

関連ノート

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