Toluene → HCID 20298674, compound

HRID 1389251Notes

Reaction equation

HRID 1389251 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].C1(C)C=CC=CC=1.[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25]Cl>CN(C)C=O>[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 20298674HCID 20298674, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-5-methoxybenzaldehyde (31.2 g) in 170 ml of dimethylformamide is treated first with 10.1 g of 50% sodium hydride, then with 160 ml of a 2 N toluene solution of 3-dimethylaminopropyl chloride, following the procedure described in Example 1A, yielding 34.1 g of the title compound, boiling point 149°-155° C. at 0.2-0.3 mm of Hg.

Sources & evidence

ORD record
ord-d38b4494522c4c14b38f1c101dcfe8ca
Source dataset
uspto-grants-1981_01
Patent number
US04243804

Reaction notes

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