HCID 12992812, compound → 3-Cyclopropoxy-4-difluoromethoxy-benzaldehyde

HRID 989450Notes

Reaction equation

HRID 989450 reaction equation
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=2[O:13][CH:14]([F:16])[F:15])[CH2:8][OH:9])[CH2:3][CH2:2]1>ClCCl.C(OCC)(=O)C.O=[Mn]=O>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=2[O:13][CH:14]([F:15])[F:16])[CH:8]=[O:9])[CH2:2][CH2:3]1

Participants

5

Reactant 1

HCID 12992812HCID 12992812, compound

Product 1

HCID 113791773-Cyclopropoxy-4-difluoromethoxy-benzaldehydeYield 75.9%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 3-Cyclopropyloxy-4-difluoromethoxybenzyl alcohol from Step 5 (41 g, 179 mmol) in dichloromethane (1.2 μL) was added MnO2 (220 g, 2.15 mol) in four portions over 2 days. When TLC indicated the reaction was complete, the mixture was diluted with ethyl acetate and filtered through Celite® (available from Aldrich Chemical Company, Inc., Milwaukee, Wis.), washing extensively with a succession of ethyl acetate, dichloromethane, EtOH and toluene. The combined filtrates were concentrated. Flash chromatography of the residue (silica gel; hexane/ethyl acetate 3:1 to 7:3) provided the 3-Cyclopropyloxy-4-difluoromethoxybenzaldehyde compound (31 g).

Workup

  1. filtrationfiltered through Celite® (available from Aldrich Chemical Company, Inc., Milwaukee, Wis.)
  2. washwashing extensively with a succession of ethyl acetate, dichloromethane, EtOH and toluene
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-66be99803a01435e8cb9fc98a0d8b3e2
Source dataset
uspto-grants-2003_10
Patent number
US06639077B2

Reaction notes

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