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

HRID 855913

Reaction equation

HRID 855913 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-58bf8e89abbc4638a914503d9c57587d
Source dataset
uspto-grants-2007_08
Patent number
US07262301B1

Linked notes

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