(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol → HCID 69203673, compound

HRID 970955Notes

Reaction equation

HRID 970955 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[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]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 69202534(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol

Product 1

HCID 69203673HCID 69203673, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)-methanol (1.15 g, 3.80 mmol) in CH2Cl2 (20 ml) at rt was added activated MnO2 powder (1.65 g, 19 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 (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(3,5-dimethoxy-phenyl)-methanone as an oil (1.06 g, 93%): 1HNMR (CDCl3) δ 7.42 (d, J=1 Hz, 1H, Ar), 7.38 (dd, J=1.88, 8 Hz, 1H, Ar), 6.92 (d, J=8 Hz, 1H, Ar), 6.88 (d, J=2 Hz, 2H, Ar), 6.64 (t, J=2 Hz, 1H, Ar), 4.36-4.29 (m, 4H, 2CH2), 3.82 (s, 6H, OCH3). The product was carried over to the next step.

Workup

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

Sources & evidence

ORD record
ord-3c9c849b9b144e36a8caaadce8e9b240
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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