Potassium Hydroxide → 3-(2-Methylphenyl)-2-propynoic acid

HRID 1594001Notes

Reaction equation

HRID 1594001 reaction equation
[OH-].[K+].Br[CH:4]([CH:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[C:5]([OH:7])=[O:6]>C(O)C>[C:10]1([CH3:15])[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]#[C:4][C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13032782HCID 13032782, compound

Product 1

HCID 127540243-(2-Methylphenyl)-2-propynoic acidYield 54.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 35.5 g of KOH in ethanol (250 ml) there were added 51.0 g (158.9 mmol) of 2,3-dibromo-3-tol-2-ylpropionic acid portionwise over a period of 30 min. The mixture was then heated under reflux over a period of 4 h. Following removal of the solvent in vacuo, the residue was taken up in 10% strength hydrochloric acid. The solution was washed with EA and then set to pH>10 with a 6N aq. NaOH solution. The mixture was then extracted with EA and the organic phase was dried over MgSO4. Following filtration and the removal of solvent in vacuo, there were obtained 13.8 g (86.2 mmol, 54%) of tol-2-ylpropiolic acid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux over a period of 4 h
  3. customremoval of the solvent in vacuo
  4. washThe solution was washed with EA
  5. extractionThe mixture was then extracted with EA
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltration
  8. customthe removal of solvent in vacuo

Sources & evidence

ORD record
ord-4f1a0be4ba81465b82a9ffd4da199863
Source dataset
uspto-grants-2007_11
Patent number
US07300939B2

Reaction notes

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