Ethyl acetate hexane → HCID 827934, compound

HRID 525838Notes

Reaction equation

HRID 525838 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH2:13][OH:14].CCOC(C)=O.CCCCCC>CCOC(C)=O.O=[Mn]=O>[OH:1][C:2]1[C:3]([CH:13]=[O:14])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 68291191HCID 68291191, compound

Product 1

HCID 827934HCID 827934, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-hydroxy-5-nitro-1,3-phenylene)dimethanol (0.50 mmol) and MnO2 (3.5 mmol) was dissolved in 2 ml EtOAc and the reaction was refluxed for 24 hours while being monitored by TLC (using EtOAc/Hexane 30:70 as eluent). The reaction mixture, once completed, was concentrated by evaporation under reduced pressure. The crude product was purified by column chromatography on silica gel (using EtOAc/Hexane 30:70 as eluent) to give 2-hydroxy-5-nitroisophthalaldehyde (40% yield) as a yellow solid.

Workup

  1. temperaturethe reaction was refluxed for 24 hours
  2. concentrationwas concentrated by evaporation under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel (using EtOAc/Hexane 30:70 as eluent)

Sources & evidence

ORD record
ord-c6640388077141318b829970f3572021
Source dataset
uspto-grants-2016_05
Patent number
US09341630B2

Reaction notes

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