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

HRID 505909Notes

Reaction equation

HRID 505909 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10]([O-:12])[CH3:11].[Na+].Cl[CH2:15][CH2:16][N:17](CC)[CH2:18][CH3:19]>C(O)C>[CH2:16]([N:17]([CH2:11][CH2:10][O:12][C:7]1[CH:8]=[CH:9][CH:2]=[CH:3][C:4]=1[CH:5]=[O:6])[CH2:18][CH3:19])[CH3:15]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 13364Diethylaminoethyl chlorideHCID 2723922Sodium ethoxide

Product 1

HCID 27645162-[2-(Diethylamino)ethoxy]benzaldehydeYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.1 g (50 mmol) of 3-hydroxybenzaldehyde were dissolved in 100 ml of ethanol and 3.5 g (50 mmol) of sodium ethanolate were added. The mixture was stirred for 15 minutes. Then 7.5 g (55 mmol) of N-(2-chloroethyl)-N,N-diethylamine were added, and the mixture was refluxed for 12 hours. The reaction mixture was then concentrated in vacuo. The residue was then partitioned between ether and 1M sodium hydroxide solution, and the ether phase was separated off, dried and concentrated in vacuo. 7.6 g of the intermediate were obtained.

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customThe residue was then partitioned between ether and 1M sodium hydroxide solution
  4. customthe ether phase was separated off
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ca48e206eb445ef872fdd79cf514fd9
Source dataset
uspto-grants-2010_08
Patent number
US07781596B1

Reaction notes

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