Propiolic Acid → HCID 14249453, compound

HRID 1651825Notes

Reaction equation

HRID 1651825 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([OH:11])(=[O:10])[C:8]#[CH:9].[CH3:12][C:13]([CH3:17])=[CH:14][CH2:15]Br>CC(C)=O>[C:7]([O:11][CH2:15][CH:14]=[C:13]([CH3:17])[CH3:12])(=[O:10])[C:8]#[CH:9]

Participants

5

Reactant 3

HCID 10110Propiolic AcidHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 14249453HCID 14249453, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

41.5 g (0.3 mol) of potassium carbonate were added at 0° to a solution of 18.4 ml (0.3 mol) of propiolic acid in 300 ml of acetone. The mixture was stirred at room temperature for 4 hours, then 34.7 ml (0.3 mol) of 3,3-dimethylallyl bromide were added and the mixture was subsequently boiled at reflux for a further 20 hours. The cooled reaction mixture was concentrated on a rotary evaporator. The residue was poured onto ice/water and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated. Distillation of the residue in a water-jet vacuum yielded 3-methyl-2-butenyl propiolate of boiling point 77°-78°/15 mmHg.

Workup

  1. temperatureat reflux for a further 20 hours
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated on a rotary evaporator
  4. additionThe residue was poured onto ice/water
  5. extractionextracted twice with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. concentrationconcentrated
  8. distillationDistillation of the residue in a water-jet vacuum

Sources & evidence

ORD record
ord-d643e26ef9024b2cbb6463a2876db550
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

Loading…