3-Hydroxybenzaldehyde → 3-[3-(dimethylamino)propoxy]benzaldehyde

HRID 259393Notes

Reaction equation

HRID 259393 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[H-].[Na+].[CH3:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16]Cl>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][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 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamine

Product 1

HCID 107270313-[3-(dimethylamino)propoxy]benzaldehydeYield 66.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The reaction between 61.0 g (0.50 mole) of 3-hydroxybenzaldehyde, 24.0 g of 50% NaH (0.50 mole), and 396 ml of 1.89N (0.75 mole) of 3-dimethylaminopropyl chloride in toluene in a procedure described for Example 2, part A, gives 69.0 g (66%) of colorless product, bp 155°-158°/3 mm.

Sources & evidence

ORD record
ord-0f9676187d514bdcbcebd258b2790717
Source dataset
uspto-grants-1977_07
Patent number
US04038274

Reaction notes

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