Benzyl Bromide → HCID 22054285, compound

HRID 1830215Notes

Reaction equation

HRID 1830215 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:25])=[C:5]([C:16]([O:23][CH3:24])=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[CH2:6][C:7]1[C:12]([CH:13]=[O:14])=[C:11]([OH:15])[CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CC(C)=O>[CH3:1][O:2][C:3]1[C:4]([CH3:25])=[C:5]([C:16]([O:23][CH3:24])=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[CH2:6][C:7]1[C:12]([CH:13]=[O:14])=[C:11]([O:15][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 21919127HCID 21919127, compound

Product 1

HCID 22054285HCID 22054285, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzaldehyde (187 mg, 0.54 mmol) was dissolved in acetone (20 ml) and after adding thereto anhydrous sodium carbonate (149 mg, 1.08 mmol) and benzyl bromide (120 mg, 0.70 mmol), the solution was stirred at room temperature for 16 hours. The reaction solution was filtered, the filtrate was concentrated and the obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=3:1) to obtain the titled compound (221 mg, 0.51 mmol, 94%).

Workup

  1. additionafter adding
  2. filtrationThe reaction solution was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-22043f604a9e4f8f864baecf2c2a4414
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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