Methanol → HCID 86739157, compound

HRID 905364Notes

Reaction equation

HRID 905364 reaction equation
[Cl:1][CH:2]([O:6][N:7]=[CH:8][C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].CO.[CH3:18]S(O)(=O)=O>ClCCCl>[Cl:1][CH:2]([O:6][N:7]=[CH:8][C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH3:18])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 86739158HCID 86739158, compound

Product 1

HCID 86739157HCID 86739157, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 12.4 gm. (0.050 mole) of 2,6-dichlorobenzylideneaminooxyacetic acid, 4.8 gm. (0.150 mole) of methanol and about 0.8 gm. of methanesulfonic acid in 15 ml. of 1,2-dichloroethane was refluxed for 15-16 hours. The cooled reaction mixture was then washed with cold, aqueous sodium bicarbonate, followed by a cold water wash. The organic phase was then concentrated under reduced pressure and at a mixture bath temperature of about 60° C. The resulting oil solidified on cooling. There were obtained 12.5 gm. (96%) of product melting at 58°-65° C. Purification by high vacuum distillation yielded material which, when allowed to crystallize, melted at 60°-62° C. (uncorrected).

Workup

  1. additionA mixture of 12.4 gm
  2. customThe cooled reaction mixture
  3. washwas then washed with cold, aqueous sodium bicarbonate
  4. washwash
  5. concentrationThe organic phase was then concentrated under reduced pressure and at a mixture bath temperature of about 60° C
  6. temperatureon cooling
  7. customThere were obtained 12.5 gm
  8. customPurification
  9. distillationby high vacuum distillation
  10. customyielded material which, when
  11. customto crystallize

Sources & evidence

ORD record
ord-da3146e6525942e4b878fc83f7669055
Source dataset
uspto-grants-1983_12
Patent number
US04423241

Reaction notes

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