2-Bromopropane → HCID 22054144, compound

HRID 1830219Notes

Reaction equation

HRID 1830219 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[CH:8]=[CH:9][C:10]([OH:15])=[C:11]([CH:14]=1)[CH:12]=[O:13].C(=O)([O-])[O-].[K+].[K+].[CH:32](Br)([CH3:34])[CH3:33]>CN(C=O)C>[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[CH:8]=[CH:9][C:10]([O:15][CH:32]([CH3:34])[CH3:33])=[C:11]([CH:14]=1)[CH:12]=[O:13]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 21919177HCID 21919177, compound

Product 1

HCID 22054144HCID 22054144, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzaldehyde (0.500 g, 1.45 mmol) was dissolved in DMF (15 ml) and after adding thereto in sequence anhydrous potassium carbonate (0.359 g, 2.60 mmol) and isopropyl bromide (0.320 g, 2.60 mmol), the solution was refluxed under heating for 3 hours. The reaction mixture was filtered, the filtrate was concentrated and the obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=4:1) to obtain the titled compound (0.530 g, 1.37 mmol, 94%).

Workup

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

Sources & evidence

ORD record
ord-d97ee71ecc7f46ee8016d06961a6fe75
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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