Sodium Carbonate → HCID 22054294, compound

HRID 1830241Notes

Reaction equation

HRID 1830241 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:27])=[C:5]([C:18]([O:25][CH3:26])=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:17])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>CC(C)=O>[CH3:1][O:2][C:3]1[C:4]([CH3:27])=[C:5]([C:18]([O:25][CH3:26])=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 79177tert-Butyl bromoacetateHCID 21919163HCID 21919163, compound

Product 1

HCID 22054294HCID 22054294, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoate (1.09 g, 2.53 mmol) was dissolved in acetone (50 ml) and after adding thereto anhydrous sodium carbonate (0.420 g, 3.03 mmol) and tert-butyl bromoacetate (0.592 g, 3.03 mmol), the solution was refluxed under heating for 3 hours. The reaction solution was filtered, the filtrate was concentrated, and the obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=2:1) to obtain the titled compound (0.650 g, 1.33 mmol, 53%).

Workup

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

Sources & evidence

ORD record
ord-e9a71a5805394247a941873346177079
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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