Acetic Anhydride → Methyl (R)-2-(4-acetylphenoxy)propionate

HRID 2392909Notes

Reaction equation

HRID 2392909 reaction equation
[O:1]([C@H:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>[Fe](Cl)(Cl)Cl.C(OCC)(=O)C>[C:14]([C:5]1[CH:6]=[CH:7][C:2]([O:1][C@H:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:3][CH:4]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 736878methyl (R)-2-phenoxypropionate

Product 1

HCID 14717335Methyl (R)-2-(4-acetylphenoxy)propionateYield 80%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 36 g (0.2 mol) of methyl (R)-2-phenoxypropionate (enantiomeric excess 94-95%), 81.6 g (0.8 mol) of acetic anhydride, 6.5 g (0.04 mol) of iron(III) chloride and 100 ml of ethyl acetate was heated at 70°-75° C. for 6 hours. The diluent and excess acetic anhydride were then removed under reduced pressure, after which the crude product was subjected to vacuum distillation. Yield: 80% (94-95% enantiomeric excess).

Workup

  1. temperaturewas heated at 70°-75° C. for 6 hours
  2. customThe diluent and excess acetic anhydride were then removed under reduced pressure
  3. distillationafter which the crude product was subjected to vacuum distillation

Sources & evidence

ORD record
ord-e53e29ac4804469c8f6fed87c071d0d1
Source dataset
uspto-grants-1998_09
Patent number
US05801272

Reaction notes

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