Sulfuric acid magnesium salt (1:1) → 4'-Methoxyacetophenone

HRID 1484396Notes

Reaction equation

HRID 1484396 reaction equation
COC1C=CC=CC=1O[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[OH:8].[O-]S([O-])(=O)=O.[Mg+2]>[Ni].CCOCC>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7](=[O:8])[CH3:6])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 54428598HCID 54428598, compound

Product 1

HCID 74764'-Methoxyacetophenone

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a vial was added wet Raney Ni 4200 (8 mg, 7×10−5 mol, 50 mol %), then 3 mL degassed hexane followed by 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol (38 mg, 1.4×10−4 mol). The vial was capped and heated to 80° C. for 24 hours. The reaction was cooled, opened and 10 mg of NH4COOH was added. 50 mL of Et2O was used to transfer the crude to an erlenmeyer containing MgSO4. After drying the solution was filtered and concentrated. HNMR gave 88% conversion to 1-(4-methoxyphenyl)ethan-1-one and only traces of 1-(4-methoxyphenyl)ethan-1-ol was detected. 88% of the β-O-4 bond was broken.

Workup

  1. custom3 mL degassed hexane
  2. customThe vial was capped
  3. temperatureThe reaction was cooled
  4. addition10 mg of NH4COOH was added
  5. customAfter drying the solution
  6. filtrationwas filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-72d44a260f4a4aafb8cd1dede2867ce9
Source dataset
uspto-grants-2016_08
Patent number
US09422215B2

Reaction notes

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