3-Hydroxybenzaldehyde → 3,3'-((2,2-Bis((3-formylphenoxy)methyl)propane-1,3-diyl)bis(oxy))dibenzaldehyde

HRID 1012367Notes

Reaction equation

HRID 1012367 reaction equation
[CH2:1](Br)[C:2]([CH2:7]Br)([CH2:5]Br)[CH2:3]Br.[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:15].[C:19](=[O:22])([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C)C=O>[CH:14]([C:13]1[CH:12]=[C:11]([CH:18]=[CH:17][CH:16]=1)[O:10][CH2:1][C:2]([CH2:7][O:10][C:11]1[CH:12]=[CH:13][CH:16]=[C:17]([CH:19]=[O:22])[CH:18]=1)([CH2:5][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH:14]=[O:15])[CH:12]=1)[CH2:3][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH:14]=[O:15])[CH:12]=1)=[O:15]

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 76701Propane, 1,3-dibromo-2,2-bis(bromomethyl)-

Product 1

HCID 873530833,3'-((2,2-Bis((3-formylphenoxy)methyl)propane-1,3-diyl)bis(oxy))dibenzaldehydeYield 85.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5 g of pentaerythrityl tetrabromide, 9.5 g of 3-hydroxybenzaldehyde, 11 g of potassium carbonate, and a catalytic amount of sodium iodide were mixed. Thereto was added dimethylformamide, to conduct reaction at 130° C. for 6 hours. After cooled, water was added thereto, and the thus-precipitated crystal was collected by filtration. Dimethylformamide was added to this crystal, and the resultant solution was filtrated. Then, methanol was added to the filtrate, and the precipitated crystal was collected by filtration (yield amount 6.1 g, and yield 85.6%).

Workup

  1. customreaction at 130° C. for 6 hours
  2. temperatureAfter cooled
  3. filtrationthe thus-precipitated crystal was collected by filtration
  4. additionDimethylformamide was added to this crystal
  5. filtrationthe resultant solution was filtrated
  6. additionThen, methanol was added to the filtrate
  7. filtrationthe precipitated crystal was collected by filtration (yield amount 6.1 g, and yield 85.6%)

Sources & evidence

ORD record
ord-85998706a5904299a8e8db1f112a5f31
Source dataset
uspto-grants-2011_07
Patent number
US07977491B2

Reaction notes

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