HCID 69203197, compound → Bis(3-ethoxy-4-methoxyphenyl)methanone

HRID 2378311Notes

Reaction equation

HRID 2378311 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH3:24])[CH:15]=2)[OH:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:23]([O:22][C:16]1[CH:15]=[C:14]([C:12]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)=[O:13])[CH:19]=[CH:18][C:17]=1[O:20][CH3:21])[CH3:24]

Participants

4

Reactant 1

HCID 69203197HCID 69203197, compound

Product 1

HCID 69205642Bis(3-ethoxy-4-methoxyphenyl)methanoneYield 85%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of bis-(3-ethoxy-4-methoxy-phenyl)-methanol (8.80 g, 26.5 mmol) in CH2Cl2 (30 mL) at room temperature was added activated MnO2 powder (11.51 g, 132 mmol) and kept adding 2˜3 equivalents of MnO2 every 3˜5 h until HPLC showed at least 98% conversion occurred. The black suspension was filtered through a Celite pad, concentrated in vacuo to give bis-(3-ethoxy-4-methoxy-phenyl)-methanone as an off-white solid (7.42 g, 85% yield): 1H NMR (CDCl3) δ 1.49 (t, J=7 Hz, 6H, 2CH2CH3), 3.96 (s, 6H, 2OCH3), 6.89-6.92 (m, 2H, Ar), 7.16 (q, J=7 Hz, 4H, 2CH2CH3), 7.35-7.42 (m, 4H, Ar). The product was used in the next step without further purification.

Workup

  1. filtrationThe black suspension was filtered through a Celite pad
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54b5a11dcf6b41699e2c3c5f1ae2a595
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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