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

HRID 1484397Notes

Reaction equation

HRID 1484397 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]>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

4

Reactant 2

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

Product 1

HCID 74764'-Methoxyacetophenone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Wet Raney Ni 4200 was dried under vacuum and carefully weight (20 mg (dry weight), 3.5×10−4 mol, 250 mol %). 4 mL degassed heptane was added, followed by 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol (38 mg, 1.4×10−4 mol). The reaction was heated at 120° C. for 24 hours. Workup: 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 100% conversion to 1-(4-methoxyphenyl)ethan-1-one, 100% of the β-O-4 bond was broken.

Workup

  1. dry with materialWet Raney Ni 4200 was dried under vacuum and carefully weight (20 mg (dry weight), 3.5×10−4 mol, 250 mol %)
  2. custom4 mL degassed heptane
  3. additionwas added
  4. temperatureWorkup: The reaction was cooled
  5. addition10 mg of NH4COOH was added
  6. customAfter drying the solution
  7. filtrationwas filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5fd995085bb94215b0081666aefdc703
Source dataset
uspto-grants-2016_08
Patent number
US09422215B2

Reaction notes

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