1-(3-Isopropoxy-4-methoxyphenyl)propanol → 3'-Isopropoxy-4'-methoxypropiophenone

HRID 41922Notes

Reaction equation

HRID 41922 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:13]([OH:16])[CH2:14][CH3:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.O=[Mn]=O>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:13](=[O:16])[CH2:14][CH3:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 667617681-(3-Isopropoxy-4-methoxyphenyl)propanol

Product 1

HCID 667609483'-Isopropoxy-4'-methoxypropiophenoneYield 94%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

A magnetically stirred solution of alcohol 4 (500 mg, 2.23 mmol) in CHCl3 (15 mL) was treated with activated MnO2 (1.94 g, 22.3 mmol) and the resulting mixture heated at reflux under a nitrogen atmosphere for 17 h. The cooled reaction mixture was filtered through a pad of Celite™ that was then washed with CHCl3 (1×15 mL). The combined filtrates were concentrated under reduced pressure to afford the title compound 10 (466 mg, 94%) as a white solid, m.p. 58.1-58.7° C.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux under a nitrogen atmosphere for 17 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through a pad of Celite™ that
  5. washwas then washed with CHCl3 (1×15 mL)
  6. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-693837eb9ab14df4abdaef443f28b03e
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

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