Acetic Acid → Methoxyacetic anhydride

HRID 487717Notes

Reaction equation

HRID 487717 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=[O:5].[C:7]([O:10][C:11](=O)[CH3:12])(=O)C.C(O)(=[O:16])C>>[CH3:1][O:2][CH2:3][C:4]([O:6][C:12](=[O:16])[CH2:11][O:10][CH3:7])=[O:5]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic Anhydride2×HCID 12251Methoxyacetic Acid

Product 1

HCID 88095Methoxyacetic anhydrideYield 71%

Procedure

A mixture of methoxyacetic acid (360 g, 4 mol) and acetic anhydride (409 g, 4 mol) was heated with stirring in a 2 L 3-neck flask equipped with a bubble-plate distillation column and a fraction cutter. A mixture of acetic acid and acetic acid anhydride was distilled at atmospheric pressure until the internal temperature reached 164° C. The pressure was reduced and the product was collected at 65°-71° C. at 0.2 mmHg to give 229 g (71%) of pure title compound. A total of 34.8 kg of methoxyacetic acid was processed to give 26.1 kg (83%) of the anhydride (I).

Workup

  1. temperaturewas heated
  2. customequipped with a bubble-plate distillation column
  3. distillationwas distilled at atmospheric pressure until the internal temperature
  4. customreached 164° C
  5. customthe product was collected at 65°-71° C. at 0.2 mmHg

Sources & evidence

ORD record
ord-9e113e3dfea049a385c48f8287ebfa40
Source dataset
uspto-grants-1994_03
Patent number
US05296589

Reaction notes

Loading…