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

HRID 2049969Notes

Reaction equation

HRID 2049969 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].CN(C)C=O.[H-].[Na+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>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][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 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 1

HCID 1140TolueneSolvent

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-e44ff88d1384475592a55f973413afac
Source dataset
uspto-grants-1980_04
Patent number
US04199528

Reaction notes

Loading…