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

HRID 2049972

Reaction equation

HRID 2049972 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH: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>[CH3:8][O:7][C:6]1[C:4]([O:5][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8991o-VanillinHCID 24758Sodium hydrideHCID 958344-(3-Chloropropyl)morpholine

Product 1

HCID 22003483-Methoxy-2-[3-(4-morpholinyl)propoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

o-Vanillin (30.4 g), dissolved in 160 ml. of dimethylformamide, is treated with 9.6 g of 50% sodium hydride, then with 130 ml. of 2 N N-(3-chloropropyl)morpholine in toluene following the procedure described in Example 1A, yielding 42.9 g of the title compound, boiling point 178°-183° C. at 0.2-0.3 mm of Hg.

Sources & evidence

ORD record
ord-a54ad57c04b84699b8be74c5cb315bac
Source dataset
uspto-grants-1980_04
Patent number
US04199528

Linked notes

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