Hexane → 4'-Methoxyacetophenone

HRID 1484395Notes

Reaction equation

HRID 1484395 reaction equation
CCCCCC.COC1C=CC=CC=1O[CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[OH:14].[BH4-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>[Ni].CCOCC>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH3:12])=[CH:16][CH:17]=1.[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH:13]([OH:14])[CH3:12])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 8058HexaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 54428598HCID 54428598, compound

Product 2

HCID 74764'-MethoxyacetophenoneHCID 1011481-(4-Methoxyphenyl)ethanol

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 hexane followed by 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol (38 mg, 1.4×10−4 mol) and of NaBH4 (3 mg, 7×10−5 mol, 50 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 63% conversion to 1-(4-methoxyphenyl)ethan-1-one and 1-(4-methoxyphenyl)ethan-1-ol in a ratio 3:7. 63% of the β-O-4 bond was broken.

Workup

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

Sources & evidence

ORD record
ord-93876dcf95944449875f43e3659363df
Source dataset
uspto-grants-2016_08
Patent number
US09422215B2

Reaction notes

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