HCID 61087120, compound → HCID 24261598, compound

HRID 2378299Notes

Reaction equation

HRID 2378299 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[OH:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 61087120HCID 61087120, compound

Product 1

HCID 24261598HCID 24261598, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(3-methoxy-phenyl)-methanol (2.08 g crude, 6.7 mmol) in CH2Cl2 (15 mL) at room temperature was added activated MnO2 powder (3.6 g, 41.4 mmol) and kept adding 23 equivalents of MnO2 every 35 h until HPLC showed disappearance of the starting material. The black suspension was filtered through a Celite pad, concentrated in vacuo to give (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(3-methoxy-phenyl)-methanone as an oil (2.0 g, 109% crude yield): 1H NMR (CDCl3) δ 3.86 (s, 3H, OCH3), 4.26-4.36 (m, 4H, CH2CH2), 6.84-7.42 (m, 7H, 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-7773934c7d8f4fd7a607e93d602cc558
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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