Sulfuric Acid → Acetic Anhydride

HRID 1606316Notes

Reaction equation

HRID 1606316 reaction equation
[OH:1]S(O)(=O)=O.[OH-].[Na+:7].[CH2:8]([O:10][C:11](=[O:21])[C@H:12](CCSC)NC(=O)C)[CH3:9].C(OCC)(=[O:24])C>C(O)(=O)C>[C:11]([O:10][C:8](=[O:24])[CH3:9])(=[O:21])[CH3:12].[OH-:1].[Na+:7]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 7018240N-acetyl-L-methionine ethyl ester3×

Product 2

HCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To this solution was added with stirring sufficient anhydrous H2SO4 to neutralize the NaOH and render the solution slightly acidic. Under these conditions the N-acetyl-L-methionine was converted to N-acetyl-L-methionine ethyl ester. The remaining ethanol and ethyl acetate (formed from the reaction of residual acetic acid and acetic anhydride with NaOH) was removed by warming the mixture under vacuum. The remaining mixture was slurried with cholorform and filtered to removed sodium sulfate salts. The ester-chloroform solution was then water washed to remove any remaining salts. The resulting ester-chloroform solution was then warmed under vacuum to remove the chloroform. The resulting material was N-acetyl-L-methionine ethyl ester.

Workup

  1. additionTo this solution was added

Sources & evidence

ORD record
ord-e851f7604cd54400a5aabb33d9d54da7
Source dataset
uspto-grants-1976_04
Patent number
US03952115

Reaction notes

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