Ammonia → Methyl 3-methyl-2-phenylbutanoate

HRID 1655762Notes

Reaction equation

HRID 1655762 reaction equation
[Na].N.[CH3:3][O:4][C:5](=[O:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:14](I)([CH3:16])[CH3:15]>O1CCCC1.[N+]([O-])([O-])=O.[Fe+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>[CH3:3][O:4][C:5](=[O:13])[CH:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:14]([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6362Isopropyl iodideHCID 7559Methyl phenylacetateHCID 5360545Sodium

Product 1

HCID 5051294Methyl 3-methyl-2-phenylbutanoateYield 87%

Reagents, catalysts & solvents 2

HCID 25251Ferric nitrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

23 g of sodium in small portions were added at -35° within 90 minutes to 1500 ml of liquid ammonia. After completion of the addition, 150 mg of iron-(III) nitrate.9H2O were added. To this suspension were added, while stirring vigorously, 150 g (1 mol) of phenylacetic acid methyl ester in 500 ml of absolute tetrahydrofuran and, half an hour later, 100 ml (1 mol) of isopropyl iodide were added dropwise. After completion of the addition, the ammonia was distilled off overnight. Water was added slowly to the liquid residue and the mixture was extracted with ether. The organic extracts were washed with water, dried over sodium sulfate and evaporated under reduced pressure, to obtain 165.8 g (87%) of 2-phenyl-3-methylbutyric acid methyl ester as a yellow oil which was used directly in the next step.

Workup

  1. addition9H2O were added
  2. additionTo this suspension were added
  3. additionAfter completion of the addition
  4. distillationthe ammonia was distilled off overnight
  5. additionWater was added slowly to the liquid residue
  6. extractionthe mixture was extracted with ether
  7. washThe organic extracts were washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b6b4b2138412438890fdab24f02a8cce
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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