Sodium Carbonate → 1,4-Benzenedicarboxaldehyde, 2,5-dihydroxy-

HRID 1471325Notes

Reaction equation

HRID 1471325 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[C:6]([O:11]C)=[CH:5][C:4]=1[CH:13]=[O:14].B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1>[OH:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[C:6]([OH:11])=[CH:5][C:4]=1[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 6066482,5-Dimethoxyterephthalaldehyde

Product 1

HCID 110842361,4-Benzenedicarboxaldehyde, 2,5-dihydroxy-

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

0.5 g of 2,5-dimethoxybenzene-1,4-dicarboaldehyde (AD) and 25 mL of boron tribromide were dissolved in 150 mL of chlorobenzene and stirred at room temperature for 12 hours. After complete reaction, the reacted mixture was neutralized with sodium carbonate, followed by extraction with water and dichloromethane and recrystallization within dichloromethane, thereby obtaining 2,5-dihydroxybenzene-1,4-dicarboaldehyde. The obtained product exhibited yield, property and NMR analysis result as follows.

Workup

  1. customAfter complete reaction
  2. extractionfollowed by extraction with water and dichloromethane and recrystallization within dichloromethane
  3. customThe obtained product exhibited yield
  4. customproperty and NMR analysis result

Sources & evidence

ORD record
ord-a7cccfe99d784838bf2079719d6825a5
Source dataset
uspto-grants-2015_04
Patent number
US09012230B2

Reaction notes

Loading…