Methyl 2-phenylthio-2-(3-phenoxyphenyl)propionate → Methyl 2-(3-phenoxyphenyl)propanoate

HRID 1660443Notes

Reaction equation

HRID 1660443 reaction equation
C1(S[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)([CH3:13])[C:9]([O:11][CH3:12])=[O:10])C=CC=CC=1>C(O)C.[Ni]>[O:20]([C:16]1[CH:15]=[C:14]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[CH:19]=[CH:18][CH:17]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 20556693Methyl 2-phenylthio-2-(3-phenoxyphenyl)propionate

Product 1

HCID 529082Methyl 2-(3-phenoxyphenyl)propanoateYield 90.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

Methyl α-phenylthio-α-(m-phenoxyphenyl)propionate (210 mg) was dissolved in 1 ml of ethanol. An ethanol suspension (5 ml) of 2 cc of Raney nickel (W-II) was added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was filtered, and the insoluble matter was washed with 50 ml of methanol. The filtrate and the washing were combined, and concentrated under reduced pressure. Methylene chloride (30 ml) was added to the residue, and the insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on a column of silica gel using benzene as an eluent to afford 134 mg of methyl α-(m-phenoxyphenyl)propionate in a yield of 90%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe insoluble matter was washed with 50 ml of methanol
  3. concentrationconcentrated under reduced pressure
  4. additionMethylene chloride (30 ml) was added to the residue
  5. customthe insoluble matter was separated by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-dedbc46eab914c4281132550406ff922
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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