Hexane → HCID 49817597, compound

HRID 84150Notes

Reaction equation

HRID 84150 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14].C([O-])(=O)C.[NH4+:22].C(OCC)(=O)C.CCCCCC>CO>[NH2:22]/[C:11](/[CH2:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[F:1])=[CH:12]\[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 29942605Methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate

Product 1

HCID 49817597HCID 49817597, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
61.5 °C

Procedure

The methyl 4-(2,4,5-trifluorophenyl)acetoacetate (350.0 gm, 1.42 mol) (21) and ammonium acetate (6.0 eq, 657.0 gm) were charged in methanol (5.0 vol, 1.75 Ltr) and the solution was refluxed for 5-6 hours at 60-63° C. After 5-6 hours refluxing, the methanol was distilled out completely to give a pale yellow coloured residue. The pale yellow coloured residue was further stirred with ethyl acetate (20.0 vol, 7.0 Ltr) at 25-30° C. The precipitated ammonium acetate was filtered and the ethyl acetate was distilled out completely to give a pale yellow product. The product was further stirred with hexane (10.0 vol, 3.5 Ltr) at 25-30° C. for 1 hour, filtered and dried under reduced pressure at 45-50° C. for 4-5 hours.

Workup

  1. temperatureAfter 5-6 hours refluxing
  2. distillationthe methanol was distilled out completely
  3. customto give a pale yellow coloured residue
  4. filtrationThe precipitated ammonium acetate was filtered
  5. distillationthe ethyl acetate was distilled out completely
  6. customto give a pale yellow product
  7. filtrationfiltered
  8. customdried under reduced pressure at 45-50° C. for 4-5 hours

Sources & evidence

ORD record
ord-0f2d1c41908b47f0bac807c35292a428
Source dataset
uspto-grants-2014_09
Patent number
US08846916B2

Reaction notes

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