Reaktion #77926

ord-7728b859049a420483ed9f879c6ba36d

Reaktionsgleichung

Cc1cc(Cl)c(S(C)(=O)=O)cc1C(=O)O
4-chloro-5-methanesulfonyl-2-methylbenzoic acid
COC(C)(OC)OC
trimethyl orthoacetate
→
COC(=O)c1cc(S(C)(=O)=O)c(S(C)(=O)=O)cc1C
methyl 4,5-bis-methanesulfonyl-2-methylbenzoate

Edukte

Cc1cc(Cl)c(S(C)(=O)=O)cc1C(=O)O
4-chloro-5-methanesulfonyl-2-methylbenzoic acid
COC(C)(OC)OC
trimethyl orthoacetate

Reagenzien

Keine

Lösungsmittel

CN1CCCC1=O
NMP

Reaktionsbedingungen

Temperatur
90°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigehad reacted completely
  2. 2
    workup.DISTILLATIONAfter the excess orthoester had been distilled off
  3. 3
    workup.ADDITION96.5 g of sodium methanesulfinate were added

Vorschrift

A solution of 100.0 g of 4-chloro-5-methanesulfonyl-2-methylbenzoic acid and 68.1 g of trimethyl orthoacetate in 322 ml of NMP was refluxed until the acid had reacted completely. After the excess orthoester had been distilled off, 96.5 g of sodium methanesulfinate were added, and the mixture was stirred at 90° C. for 18 h. Conventional work-up gave methyl 4,5-bis-methanesulfonyl-2-methylbenzoate.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06706921B2uspto-grants-2004_03