Sodium hydride → 4-Methoxy-2-[3-(4-morpholinyl)propoxy]benzaldehyde

HRID 263108Notes

Reaction equation

HRID 263108 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([O:1][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 958344-(3-Chloropropyl)morpholine

Product 1

HCID 202986814-Methoxy-2-[3-(4-morpholinyl)propoxy]benzaldehydeYield 65.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4-methoxybenzaldehyde (25 g) in 125 ml of dimethylformamide is treated first with 8.2 g of 50% sodium hydride, then with 36 g of N-(3-chloropropyl)morpholine dissolved in 65 ml of toluene, following the procedure described in Example 1A, yielding 30.2 g of the title compound, boiling point 190°-195° C. at 0.1-0.2 mm of Hg.

Sources & evidence

ORD record
ord-2169c8994458464fbf597f6fb6fd74e1
Source dataset
uspto-grants-1979_05
Patent number
US04156079

Reaction notes

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