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

HRID 1891435노트

반응식

HRID 1891435 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f25129960c8749978fe560efd389dfba
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507549B2

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