Diethyl Ether → Methyl 2-(3-phenoxyphenyl)propanoate

HRID 1660441Notes

Reaction equation

HRID 1660441 reaction equation
CS[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C(OCC)C>C(O)(=O)C.S([O-])([O-])(=O)=O.[Cu+2].[Zn]>[O:15]([C:11]1[CH:10]=[C:9]([CH:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])[CH:14]=[CH:13][CH:12]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 3283Diethyl EtherHCID 12917662Methyl alpha-methylthio-alpha-(m-phenoxyphenyl)propionate

Product 1

HCID 529082Methyl 2-(3-phenoxyphenyl)propanoateYield 97.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl α-methylthio-α-(m-phenoxyphenyl)propionate (302 mg) was dissolved in 2 ml of acetic acid, and 16 mg of anhydrous copper sulfate and 150 mg of zinc powder were added. With stirring, the mixture was heated under reflux for 9 hours. Furthermore, 50 mg of zinc powder was added, and the mixture was heated under reflux for 2 hours. Diethyl ether (60 mg) was added, and the insoluble matter was separated by filtration. The filtrate was washed twice with 10 ml of water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to short-path distillation (bath temperature 140°-160° C./0.02 mmHg) to afford 249 mg of methyl α-(m-phenoxyphenyl)propionate as a colorless oil in a yield of 97%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 9 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2 hours
  5. customthe insoluble matter was separated by filtration
  6. washThe filtrate was washed twice with 10 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. distillationthe residue was subjected to short-path distillation (bath temperature 140°-160° C./0.02 mmHg)

Sources & evidence

ORD record
ord-f1ce4b247b244285909474b21483d732
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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