2-Amino-m-cresol → 2-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol

HRID 2213987Notes

Reaction equation

HRID 2213987 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:12][O:13][CH3:14])=[C:7]([CH:10]=1)[CH:8]=O.[NH2:15][C:16]1[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:23]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:12][O:13][CH3:14])=[C:7]([CH:10]=1)[CH:8]=[N:15][C:16]1[C:17]([CH3:23])=[CH:18][CH:19]=[CH:20][C:21]=1[OH:22]

Participants

4

Reactant 2

HCID 30141382-Amino-m-cresolHCID 114355225-Methoxy-2-(methoxymethoxy)benzaldehyde

Product 1

HCID 219593232-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenolYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5-methoxy-2-methoxymethoxybenzaldehyde (F1) (2.77 g, 16.5 mmol) and 2-amino-m-cresol (2.03 g, 16.5 mmol) in benzene (70 mL) was refluxed for 15 h using an additional funnel to remove water. After the reaction mixture was cooled to room temperature, the solvent was removed in vacuo and the resulting residue was washed with ethanol to afford the objective compound as a orange solid (84%), which was used for next reaction without further purification: 1H-NMR 400 MHz, DMSO-d6) δ2.31 (s, 3H), 3.45 (s, 3H), 3.85 (s, 3H), 5.18 (s, 2H), 6.59 (s, 1H), 6.77 (d, 1H, J=8.0 Hz), 6.83 (d, 1H, J=8.0 Hz), 6.99 (t, 1H, J=8.0 Hz), 7.03 (dd, 1H, J=9.0, 2.5 Hz), 7.14 (d, 1H, J=9.0 Hz), 7.68 (s, 1H), 8.95 (s, 1H).

Workup

  1. customto remove water
  2. customthe solvent was removed in vacuo
  3. washthe resulting residue was washed with ethanol

Sources & evidence

ORD record
ord-a78a27811d114a84be29d68486ed1c88
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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