Hexane → 2-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]acetoaldehyde

HRID 1588125Notes

Reaction equation

HRID 1588125 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:9]([O:10][CH2:11][O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=[C:6]([O:16][CH2:17][O:18][CH3:19])[C:5]=1[O:20][CH3:21].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>ClCCl>[CH3:21][O:20][C:5]1[C:6]([O:16][CH2:17][O:18][CH3:19])=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:10][CH2:11][O:12][CH3:13])[C:4]=1[CH2:3][CH:2]=[O:1]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 137145691-(2-Hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzeneHCID 178418287HCID 178418287, compound

Product 1

HCID 197572302-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]acetoaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.3 Grams (4.3 mM) of 1-(2-hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene was dissolved in 15 ml of dichloromethane, then under ice-cooling condition, 1 g of pyridinium chlorochromate was added thereto and the reaction mixture was stirred at a room temperature for 10 hours. After filtration, the filtrate was concentrated under a reduced pressure, and the residue obtained was treated by a silica gel column chromatography (diameter 3 cm×length 15 cm, eluent: 30% ethyl acetate: n-hexane, "Wakogel C-200") to yield 1 g of 2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]acetoaldehyde. Colorless oily substance.

Workup

  1. additionwas added
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customthe residue obtained

Sources & evidence

ORD record
ord-41392c5708d840f6bd3f60cacef3ccc3
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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