Benzyl Bromide → HCID 18461312, compound

HRID 2303913Notes

Reaction equation

HRID 2303913 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([O:18][C:19]1[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([OH:29])=[CH:21][C:20]=1[C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:17])[CH3:16]>CC(C)=O>[C:15]([O:18][C:19]1[CH:24]=[C:23]([C:25]([CH3:26])([CH3:28])[CH3:27])[C:22]([O:29][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:21][C:20]=1[C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 53998699HCID 53998699, compound

Product 1

HCID 18461312HCID 18461312, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (5.17 g) and potassium carbonate (4.15 g) were added to a solution of 2,5-di-t-butyl-4-hydroxyphenyl acetate (5.3 g) in acetone (40 ml). The mixture was stirred at ambient temperature for 48 hours. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was dried over anhydrous sodium sufate and concentrated. The residue was purified by chromatography on a silica gel column using c-hexane/diisopropyl ether=10/1 as the eluant to give the title compound (4.9 g).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sufate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-7f7549e211854708853c0af6a4833741
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

Loading…