Benzyl Bromide → (4-Benzyloxy-2-hydroxy-phenyl)-(4-benzyloxy-phenyl)-methanone

HRID 1891435ノート

反応式

HRID 1891435 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O>[CH2:24]([O:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:9][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=3)=[CH:13][CH:12]=2)=[O:10])=[C:2]([OH:1])[CH:7]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 738522,4,4'-Trihydroxybenzophenone

生成物 1

HCID 67497980(4-Benzyloxy-2-hydroxy-phenyl)-(4-benzyloxy-phenyl)-methanone収率 119.9%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a suspension of (2,4-dihydroxy-phenyl)-(4-hydroxy-phenyl)-methanone (9.2 g, 40 mmol) and oven dried potassium carbonate (11.6 g, 84 mmol) in acetone refluxing at 60° C., was added benzyl bromide (10 mL, 83 mmol) in two portions of 5 mL each, dropwise. The reaction was refluxed for 12 hours and solids were filtered and washed with 100 ml of CH7Cl2. The solvents combined and evaporated to give yellow product along with some tribenzylated side product, which was recrystallized from CH2Cl2:hexane (1:5) to get (9.84 g, 60%) of pure product T1. 1H NMR (400 MHz, DMSO-d6) δ, 7.4 (m, 12H, Ar—H2′/6′, 2×C6H5), 6.97 (m, 3H, Ar—H3′/5′, Ar—H6), 5.84 (d, 1H, Ar—H3), 5.6 (dd, 1H, Ar—H5), 5.14 (s, 2H, PhCH2), 4.94 (s, 2H, PhCH2).

後処理

  1. temperatureThe reaction was refluxed for 12 hours
  2. filtrationsolids were filtered
  3. washwashed with 100 ml of CH7Cl2
  4. customevaporated
  5. customto give yellow product along with some tribenzylated side product, which
  6. customwas recrystallized from CH2Cl2:hexane (1:5)

出典と根拠

ORDレコード
ord-f25129960c8749978fe560efd389dfba
出典データセット
uspto-grants-2013_08
特許番号
US08507549B2

反応ノート

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