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

HRID 259392

Reaction equation

HRID 259392 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]([CH3:17])[CH2:14][CH2:15]Cl>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydride

Product 1

HCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeYield 46.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The reaction between 61.0 g (0.50 mole) of 4-hydroxybenzaldehyde, 24.0 g of 50% NaH, and 341 ml of 2.2 N (0.75 mole) 2-dimethylaminoethyl chloride in toluene in a procedure described for Example 2,part A, gives 45.0 g (46%) of colorless product, bp 140°-142°/2 mm. Lit. bp 185°-187°/15 mm.

Sources & evidence

ORD record
ord-a2ddb5f051504bd5afee04ff26e57a22
Source dataset
uspto-grants-1977_07
Patent number
US04038274

Linked notes

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