2,5-Dimethoxybenzaldehyde → 2-[(2,5-Dimethoxybenzylidene)amino]-3-methylphenol

HRID 2213990Notes

Reaction equation

HRID 2213990 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20]OC)=[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].COC1C=CC(OC)=CC=1C=O>>[CH3:20][O:19][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][C:7]=1[CH:8]=[N:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[OH:17]

Participants

3

Reactant 2

HCID 667262,5-DimethoxybenzaldehydeHCID 219593232-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol

Product 1

HCID 219593342-[(2,5-Dimethoxybenzylidene)amino]-3-methylphenol

Procedure

2-[(2,5-dimethoxybenzylidene)amino]-3-methylphenol (F7) was prepared in a similar manner for the preparation of 2-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol (F4) by using 2,5-dimethoxybenzaldehyde (3.32 g, 20 mmol) instead of 5-methoxy-2-methoxymethoxybenzaldehyde (F1) in 82% (4.44 g): 1H-NMR (400 MHz, CDCl3) δ2.32 (s, 3H), 3.84 (s, 6H), 6.77 (d, 1H, J=7.6 Hz), 6.82 (d, 1H, J=2.0 Hz), 6.83 (d, 1H, J=7.6 Hz), 6.91 (d, 1H, J=9.2 Hz), 6.99 (t, 1H, J=7.6 Hz), 7.06 (dd 1H, J=9.2, 2.0 Hz), 7.69 (s, 1H), 8.94 (s, 1H).

Sources & evidence

ORD record
ord-a5bd40493ca54e359f3b56ed6a06bfa6
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

Loading…