tert-Butanol → 1-Allenyloxy benzene-4-carboxylic acid

HRID 1742732

Reaction equation

HRID 1742732 reaction equation
CC([O-])(C)C.[K+].CC(O)(C)C.[CH2:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1)[C:13]#[CH:14]>O>[CH:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1)=[C:13]=[CH2:14]

Participants

5

Reactant 3

HCID 6386tert-Butanol2×HCID 30892004-(Prop-2-yn-1-yloxy)benzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 145964421-Allenyloxy benzene-4-carboxylic acidYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a similar reaction vessel, as used in the abovementioned reaction, were placed 7.920 parts of t-BuOK and 44.882 parts of t-BuOH and to this, a mixture of 10,000 parts of 1-propargyloxybenzene-4-carboxylic acid and 23.333 parts of t-BuOH was added dropwise. The content was reacted at 50° C. for 60 minutes and then a deionized water was added to stop the reaction. t-BuOH layer and water layer were removed by using an evaporator, and the residue was added with 1N-HCl and then extracted with an ether. The ether solvent was removed and the residue was subjected to a column chromatography (silica gel 200 mesh) to obtain a purified 1-allenyloxy benzene-4-carboxylic acid as a colorless clear oily product. This compound was identified by FT-NMR(H) and IR spectrum. The reaction yield was 43.0%.

Workup

  1. customInto a similar reaction vessel, as used in the abovementioned reaction
  2. additionwas added dropwise
  3. customThe content was reacted at 50° C. for 60 minutes
  4. customthe reaction
  5. customt-BuOH layer and water layer were removed
  6. customan evaporator
  7. additionthe residue was added with 1N-HCl
  8. extractionextracted with an ether
  9. customThe ether solvent was removed

Sources & evidence

ORD record
ord-bf009f3cc30744d3ac1b7b060a19d4fc
Source dataset
uspto-grants-1994_08
Patent number
US05340931

Linked notes

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