Diethyl Ether → Methyl alpha-(m-phenoxyphenyl)isovalerate

HRID 1733622Notes

Reaction equation

HRID 1733622 reaction equation
CS[C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=1)([CH:8]([CH3:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5].C(OCC)C>C(O)(=O)C.S([O-])([O-])(=O)=O.[Cu+2].[Zn]>[O:17]([C:13]1[CH:12]=[C:11]([CH:3]([CH:8]([CH3:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])[CH:16]=[CH:15][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 2

HCID 3283Diethyl EtherHCID 20556695Methyl alpha-methylthio-alpha-(m-phenoxyphenyl)isovalerate

Product 1

HCID 20556701Methyl alpha-(m-phenoxyphenyl)isovalerateYield 88%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl α-methylthio-α-(m-phenoxyphenyl)isovalerate (702 mg) was dissolved in 5 ml of acetic acid, and 50 mg of anhydrous copper sulfate and 500 mg of zinc powder was added. The mixture was heated under reflux for 23 hours. Diethyl ether (80 ml) was added, and the insoluble matter was separated by filtration. The filtrate was washed twice with 25 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using benzene as an eluent to afford 531 mg of methyl α-(m-phenoxyphenyl)isovalerate in a yield of 88%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 23 hours
  3. customthe insoluble matter was separated by filtration
  4. washThe filtrate was washed twice with 25 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-c04efaccf0c142bd835a3834f9eff272
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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