Cuminaldehyde → HCID 24786789, compound

HRID 1360637Notes

Reaction equation

HRID 1360637 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][NH2:16].O>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N:16][CH2:15][CH:14]([O:17][CH3:18])[O:13][CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 326CuminaldehydeHCID 962WaterHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 24786789HCID 24786789, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-isopropyl benzaldehyde (25 g, 183 mmol) and aminoacetaldehyde dimethylacetal (28.9 g, 275 mmol) in toluene (250 ml) was refluxed with azeotropic removal of water for 13 hours. The solvent was removed under vacuum to afford the titled compound as viscous oil (36 g, 83%). TLC-Chloroform/methanol: (95/5): Rf=0.75. 1H-NMR (CDCl3, 400 MHz) δ 1.28 (6H, d), 2.95 (1H, m), 3.44 (6H, s), 3.78 (2H, d), 4.68 (1H, t), 7.28 (2H, d), 7.68 (2H, d), 8.27 (1H, s).

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e1e1dc7a863f4be4b987f2de4e05063f
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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