4-Hydroxybenzaldehyde → 4-[3-(Dimethylamino)propoxy]benzaldehyde

HRID 918205Notes

Reaction equation

HRID 918205 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16]Cl>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamine

Product 1

HCID 5469324-[3-(Dimethylamino)propoxy]benzaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 61.0 g (0.50 mole) of 4-hydroxybenzaldehyde in 400 ml of dimethylformamide (nitrogen atmosphere) is gradually treated with 24.0 g of 50% NaH. The temperature is kept below 35° using an ice water bath. When the addition is completed, the thick mixture is heated to 70° for several minutes, then cooled to 35° before the addition of 417 ml of 1.8N (0.75 mole) of 3-dimethylaminopropyl chloride in toluene.

Workup

  1. customis kept below 35°
  2. additionWhen the addition
  3. temperaturethe thick mixture is heated to 70° for several minutes

Sources & evidence

ORD record
ord-74d760df930e4d169c928827da131f49
Source dataset
uspto-grants-1976_07
Patent number
US03969527

Reaction notes

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