Carbon Dioxide → 4-(2-Methylphenoxy)butyl propiolate

HRID 1441155Notes

Reaction equation

HRID 1441155 reaction equation
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].C(=O)(O)[O-].[Na+].C(=O)=O.[CH3:14][C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21]Br>CO.CN(C)C=O>[C:1]([O:5][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:16]1[CH:23]=[CH:24][CH:25]=[CH:26][C:15]=1[CH3:14])(=[O:4])[C:2]#[CH:3]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 10110Propiolic AcidHCID 516892Sodium BicarbonateHCID 47390421-(4-Bromobutoxy)-2-methylbenzene

Product 1

HCID 153350284-(2-Methylphenoxy)butyl propiolateYield 37.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 10 g of propiolic acid, 12 g of anhydrous sodium bicarbonate in 150 ml of anhydrous methanol was heated to 40° C. with stirring. When evolution of carbon dioxide ceased, the reaction mixture was cooled to a temperature 10° C. or less. The resultant precipitate was collected and dried under reduced pressure for two days. A mixture of 1 g of the sodium propiolate thus obtained and 2.64 g of 4-(2-methylphenoxy)butyl bromide in 30 ml of anhydrous N,N-dimethylformamide was heated at 110° C. under nitrogen atmosphere for four hours with stirring. After the reaction was completed, the reaction solution was poured into ice-water, and extracted twice with toluene. The combined toluene layer was washed successively with a saturated aqueous ammonium chloride solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained residue was subjected to silicagel column chromatography to yield 0.937 g of 4-(2-methylphenoxy)butyl propiolate (compound 10).

Workup

  1. temperaturethe reaction mixture was cooled to a temperature 10° C. or less
  2. customThe resultant precipitate was collected
  3. customdried under reduced pressure for two days
  4. additionA mixture of 1 g of the sodium propiolate
  5. customthus obtained
  6. stirringwith stirring
  7. extractionextracted twice with toluene
  8. washThe combined toluene layer was washed successively with a saturated aqueous ammonium chloride solution
  9. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  10. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-336f2835944d4211b2e619bf776b22d1
Source dataset
uspto-grants-1996_03
Patent number
US05502242

Reaction notes

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