(3-ethoxy-4-methoxy-phenyl)-(1-methyl-1H-benzotriazol-5-yl)-methanol → (3-ethoxy-4-methoxy-phenyl)-(1-methyl-1H-benzotriazol-5-yl)-methanone

HRID 2377133Notes

Reaction equation

HRID 2377133 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([C:14]2[CH:23]=[CH:22][C:17]3[N:18]([CH3:21])[N:19]=[N:20][C:16]=3[CH:15]=2)[OH:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]([C:14]2[CH:23]=[CH:22][C:17]3[N:18]([CH3:21])[N:19]=[N:20][C:16]=3[CH:15]=2)=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

4

Reactant 1

HCID 68939793(3-ethoxy-4-methoxy-phenyl)-(1-methyl-1H-benzotriazol-5-yl)-methanol

Product 1

HCID 68940515(3-ethoxy-4-methoxy-phenyl)-(1-methyl-1H-benzotriazol-5-yl)-methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of (3-ethoxy-4-methoxy-phenyl)-(1-methyl-1H-benzotriazol-5-yl)-methanol from above and MnO2 (2.5 g, 29 mmol) in methylene chloride (40 mL) was stirred at room temperature for 18 h. More MnO2 (1.5 g) was added and kept for overnight. The suspension was filtered thru a pad of Celite. Removal of solvent gave (3-ethoxy-4-methoxy-phenyl)-(1-methyl-1H-benzotriazol-5-yl)-methanone as an off-white solid (1.12 g, 58% yield 2 step): 1H NMR (CDCl3) δ 1.49 (t, J=7 Hz, 3H, CH3), 3.97 (s, 3H, CH3), 4.17 (q, J=7 Hz, 2H, CH2), 4.36 (s, 3H, CH3), 6.91 (d, J=8 Hz, 1H, Ar), 7.40 (dd, J=2, 8 Hz, 1H, Ar), 7.50 (d, J=2 Hz, 1H, Ar), 7.62 (d, J=8 Hz, 1H, Ar), 8.04 (dd, J=2, 9 Hz, 1H, Ar), 8.44-8.45 (m, 1H, Ar).

Workup

  1. waitkept for overnight
  2. filtrationThe suspension was filtered
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-77fedf2d51ca486f864db96e6eab165a
Source dataset
uspto-grants-2008_12
Patent number
US07468446B2

Reaction notes

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