tert-Butanol → Benzoic Acid

HRID 1609338Notes

Reaction equation

HRID 1609338 reaction equation
C1(C2N=C(/C=C/[C:12]3[CH:13]=[C:14]([CH:18]=[O:19])[CH:15]=[CH:16][CH:17]=3)SC=2)CCC1.CC(C)([O-:23])C.[K+].C(O)(C)(C)C>C(O)(=O)C>[C:18]([OH:19])(=[O:23])[C:14]1[CH:13]=[CH:12][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 9838296HCID 9838296, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture composed of 3.15 g of (E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzenecarboxaldehyde, 1.44 g of potassium tert-butoxide and 100 ml of tert-butanol was heated to reflux for 2 hr while exposed to air. The mixture was then diluted with 100 ml of ice water. This mixture was then acidified with acetic acid and extracted with methylene chloride. The combined extracts were washed with water, brine, dried (MgSO4) and concentrated in vacuo to yield (E)-3-[2-(4-cyclobutyl)-2-thiazolyl)ethenyl]benzoic acid; m.p. 172°-175° C. from ethyl acetate.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hr while exposed to air
  3. extractionextracted with methylene chloride
  4. washThe combined extracts were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57923a32bf8749e080820117379a452c
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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