Hydrochloride methanol → 4-Dimethylaminomethylbenzaldehyde

HRID 907799Notes

Reaction equation

HRID 907799 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=1)C.Cl.CO>CO>[CH3:14][N:12]([CH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=1)[CH3:13]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 230003481-(4-(Diethoxymethyl)phenyl)-n,n,-dimethylmethanamine

Product 1

HCID 1932514-DimethylaminomethylbenzaldehydeYield 104.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-(diethoxymethyl)phenyl)-N,N,-dimethylmethanamine (1.0 g, 4 mmol) in methanol (5 mL), a hydrochloric acid-methanol solution (10 mL) was added dropwise at 0° C. The reaction solution was stirred at room temperature overnight. Then methanol was removed in vacuo to give 4-((dimethylamino)methyl)benzaldehyde (0.68 g, yield 99%) as a light yellow oil. 1H-NMR (400 MHz, CDCl3): δ 2.26 (s, 6H), 3.50 (s, 2H), 7.49 (d, J=6.4 Hz, 2H), 7.84 (d, J=6.4 Hz, 2H), 10 (s, 1H). LC-MS (ESI) m/z: 164 (M+1)+.

Workup

  1. customThen methanol was removed in vacuo

Sources & evidence

ORD record
ord-d00f4c31b2f04b1f9f5d7645e04a77c4
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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