Sulfuric Acid → Methyl Acetate

HRID 1658168Notes

Reaction equation

HRID 1658168 reaction equation
[OH:1]S(O)(=O)=O.[OH-].[Na+:7].C(N[CH:12]([C:17]([OH:19])=[O:18])CCSC)(=O)C.[CH3:20][O:21][C:22](=[O:32])[CH:23](CCSC)NC(=O)C>C(O)(=O)C.CO>[C:22]([O:21][CH3:20])(=[O:32])[CH3:23].[C:22]([O:19][C:17](=[O:18])[CH3:12])(=[O:21])[CH3:23].[OH-:1].[Na+:7]

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 6180N-Acetyl-DL-methionineHCID 14798Sodium HydroxideHCID 53721635671-83-1

Product 3

HCID 6584Methyl AcetateHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

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-D,L-methionine was converted to N-acetyl-D,L-methionine methyl ester. The remaining methanol and methyl 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 chloroform 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-D,L-methionine methyl ester.

Workup

  1. additionTo this solution was added

Sources & evidence

ORD record
ord-cd4aff3830af44b29d99989104a64b1a
Source dataset
uspto-grants-1976_06
Patent number
US03963573

Reaction notes

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