4,5-Dimethoxy-2-methoxymethoxybenzaldehyde → 2-[(4,5-Dimethoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol

HRID 2213988Notes

Reaction equation

HRID 2213988 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20][O:21][CH3:22])=[C:7]([CH:18]=1)[CH:8]=[N:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[OH:17].[CH3:23][O:24]C1C(OC)=CC(C=O)=C(OCOC)C=1>>[CH3:23][O:24][C:4]1[C:3]([O:2][CH3:1])=[CH:18][C:7]([CH:8]=[N:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[OH:17])=[C:6]([O:19][CH2:20][O:21][CH3:22])[CH:5]=1

Participants

3

Reactant 2

HCID 219593224,5-Dimethoxy-2-methoxymethoxybenzaldehydeHCID 219593232-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol

Product 1

HCID 219593132-[(4,5-Dimethoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol

Procedure

2-[(4,5-dimethoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol (F5) was prepared in a similar manner for the preparation of 2-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol (F4) by using 4,5-dimethoxy-2-methoxymethoxybenzaldehyde (F2) (2.26 g, 10 mmol) instead of 5-methoxy-2-methoxymethoxybenzaldehyde (F1) in 86% (2.80 g): 1H-NMR (500 MHz, CDCl3) δ3.53 (s, 3H), 5.24 (s, 3H), 7.17 (d, 1H, J=9.0 Hz), 7.35 (d, 1H, J=9.0 Hz), 10.52 (s, 1H).

Sources & evidence

ORD record
ord-568765deeac74bb3b38bd23ee461406a
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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