Methanol → HCID 53942064, compound

HRID 971387Notes

Reaction equation

HRID 971387 reaction equation
[C:1]([C:9]1[S:13][CH:12]=[C:11]([CH2:14][C:15]([OH:17])=[O:16])[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]O>>[C:1]([C:9]1[S:13][CH:12]=[C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 21313692HCID 21313692, compound

Product 1

HCID 53942064HCID 53942064, compound

Procedure

9.8 gm of raw 5-benzoyl-thiophene-3-acetic acid were dissolved in 150 cc of methanol. A stream of gaseous hydrochloric acid was bubbled through this solution until the same was saturated. The methanol was evaporated and the residue was taken up in ether. The ethereal phase was washed with an aqueous 10% potassium carbonate solution, then with water until the wash waters were neutral. Thereafter, the ethereal phase was dried over magnesium sulfate, treated with carbon black, filtered and the ether was evaporated. After distillation, 5.45 gm of methyl 5-benzoyl-thiophene-3-acetate were obtained in the form of a colorless liquid, soluble in ether and insoluble in water, boiling at 170° -172° C. under 0.2 mm of Hg.

Workup

  1. customA stream of gaseous hydrochloric acid was bubbled through this solution until the
  2. customThe methanol was evaporated
  3. washThe ethereal phase was washed with an aqueous 10% potassium carbonate solution
  4. dry with materialThereafter, the ethereal phase was dried over magnesium sulfate
  5. additiontreated with carbon black
  6. filtrationfiltered
  7. customthe ether was evaporated
  8. distillationAfter distillation

Sources & evidence

ORD record
ord-c2ac3387a14a4730b745ac2a1b6027b0
Source dataset
uspto-grants-1979_07
Patent number
US04159986

Reaction notes

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