3-Hydroxybenzaldehyde → 3-[2-(dimethylamino)ethoxy]benzaldehyde

HRID 619167Notes

Reaction equation

HRID 619167 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].Cl.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20]Cl>CN(C=O)C>[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 108216053-[2-(dimethylamino)ethoxy]benzaldehydeYield 16.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-hydroxybenzaldehyde (5.44 g, 44.55 mmol), K2CO3 (13.6 g) and DMF (50 ml) was added in portions 2-dimethylaminoethylchloride hydrochloride (7.1 g). The reaction mixture was stirred at room temperature overnight, filtered and the filtrate was stripped. The residue was diluted with 1N HCl (300 ml), and extracted with ether, and the ether layer was dried over MgSO4 and stripped. The acidic aqueous layer was cooled and then treated with 8N NaOH till basic, then it was extracted with ether (3×150 ml). The ether layers were combined, dried over MgSO4, filtered and stripped to afford, as an oily liquid, 1.43 g of 3-[2-(dimethylamino)ethoxy]benzaldehyde.

Workup

  1. filtrationfiltered
  2. additionThe residue was diluted with 1N HCl (300 ml)
  3. extractionextracted with ether
  4. dry with materialthe ether layer was dried over MgSO4
  5. temperatureThe acidic aqueous layer was cooled
  6. additiontreated with 8N NaOH till basic, then it
  7. extractionwas extracted with ether (3×150 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-3d599c500a9547749a388509bca0ab1a
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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