HCID 384224, compound → HCID 24820230, compound

HRID 2378308Notes

Reaction equation

HRID 2378308 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[OH:11])=[CH:9][C:4]=2[O:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 1

HCID 384224HCID 384224, compound

Product 1

HCID 24820230HCID 24820230, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of benzo[1,3]dioxol-5-yl-(4-methoxy-phenyl) -methanol (2.54 g crude, 9.1 mmol) in CH2Cl2 (20 mL) at room temperature was added activated MnO2 powder (4.0 g, 45.5 mmol) and kept adding 2˜3 equivalents of MnO2 every 3˜5 h until HPLC showed disappearance of the starting material. The black suspension was filtered through a Celite pad, concentrated in vacuo to give benzo[1,3]dioxol-5-yl-(4-methoxy-phenyl)-methanone as a yellow solid (2.47 g, 106% crude yield, HPLC purity 93%): 1H NMR (CDCl3) δ 3.89 (s, 3H, —OCH3), 6.06 (s, 2H, CH2), 6.76-6.98 (m, 3H, Ar), 7.26-7.39 (m, 2H, Ar), 7.75-7.80 (m, 2H, 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-8c71cd3c5b414105a865beeba7cb78e6
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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