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

HRID 1891435Notes

Reaction equation

HRID 1891435 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f25129960c8749978fe560efd389dfba
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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