4-Hydroxybenzaldehyde → p-(2-(Dimethylamino)ethoxy)benzaldehyde

HRID 703525Notes

Reaction equation

HRID 703525 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19]Cl.C(OC(C)C)(C)C>CN(C)C=O.O>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 79012-Chloro-N,N-dimethylethylamineHCID 7914Diisopropyl EtherHCID 11430Potassium Carbonate

Product 1

HCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeYield 71.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 61.1 g of p-hydroxybenzaldehyde in 240 ml of N,N-dimethylformamide was added 138 g of potassium carbonate, 80.7 g of 2-dimethylaminoethyl chloride and 30 ml of isopropyl ether. The mixture was stirred at 60° C. for 1.5 hours. After cooling, the reaction mixture was poured into 720 ml of water, and the whole was extracted with chloroform. The chloroform layer was extracted with aqueous hydrochloric acid. The aqueous layer was made alkaline with aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was distilled to give 69.1 g of colorless oil, b.p. 142°-144° C. (4 mmHg).

Workup

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with chloroform
  3. extractionThe chloroform layer was extracted with aqueous hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-aba9b1ab47284d8baf0d2e74d53d3fa9
Source dataset
uspto-grants-1991_01
Patent number
US04983633

Reaction notes

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