2,4-Dihydroxybenzaldehyde → HCID 19104790, compound

HRID 1197761Notes

Reaction equation

HRID 1197761 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl[CH2:12][CH2:13][N:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium Carbonate

Product 1

HCID 19104790HCID 19104790, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture containing 0.8 mole of 2,4-dihydoxy-benzaldehyde, 0.8 mole of 2-chloro-1-dimethylaminoethane and 1.6 mole of potassium carbonate in 1200 ml of anhydrous methyl ethyl ketone is refluxed for 1 hour 30 minutes with stirring. After cooling, the precipitate formed is filtered and washed with methyl ethyl ketone. The filtrate is then evaporated and leads to a brown oil which is purified by chromatography of a silica column using a dichloromethane-methanol mixture (90/10) as eluting solvent. The expected product is then obtained after recrystallization from isopropanol.

Workup

  1. temperatureis refluxed for 1 hour 30 minutes
  2. temperatureAfter cooling
  3. customthe precipitate formed
  4. filtrationis filtered
  5. washwashed with methyl ethyl ketone
  6. customThe filtrate is then evaporated
  7. customis purified by chromatography of a silica column
  8. washas eluting solvent

Sources & evidence

ORD record
ord-90c4624a5a3541ab8406da44b989d38d
Source dataset
uspto-grants-1994_01
Patent number
US05278154

Reaction notes

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