Acetic Acid → HCID 13972066, compound

HRID 1079028Notes

Reaction equation

HRID 1079028 reaction equation
O=[O+][O-].[C:4]1([CH2:10][O:11][C:12](=[O:18])[CH:13]([CH3:17])[CH2:14][CH:15]=C)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O=O.C(O)(=[O:23])C>CO.[Zn]>[C:4]1([CH2:10][O:11][C:12](=[O:18])[CH:13]([CH3:17])[CH2:14][CH:15]=[O:23])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 24823Ozone2×HCID 11735856Racemic 2-methyl-4-pentenoic acid phenylmethyl ester

Product 1

HCID 13972066HCID 13972066, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A stream of ozone is passed through a -78° C. solution of 1.0 g of racemic 2-methyl-4-pentenoic acid phenylmethyl ester in 110 ml of methyl alcohol until the blue color persists. The excess ozone is discharged by a stream of oxygen, followed by argon. One gram of zinc dust and 1.0 g of acetic acid is added and the resulting mixture allowed to warm to room temperature; followed by stirring for 1 hour. The excess zinc is removed by filtration and the filtrate is concentrated in vacuo. The residue is extracted with diethyl ether, filtered and the filtrate concentrated in vacuo. The residue is purified by pad filtration (silica gel, 50% diethyl ether/petroleum ether) to give 1.01 g of racemic 2-methyl-4-oxobutanoic acid phenylmethyl ester.

Workup

  1. customis passed through a -78° C.
  2. customThe excess zinc is removed by filtration
  3. concentrationthe filtrate is concentrated in vacuo
  4. extractionThe residue is extracted with diethyl ether
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. filtrationThe residue is purified by pad filtration (silica gel, 50% diethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-3c152679880240d89160fb6aa22aaf85
Source dataset
uspto-grants-1996_08
Patent number
US05550257

Reaction notes

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