Water → Benzyl propiolate

HRID 653950Notes

Reaction equation

HRID 653950 reaction equation
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].C(=O)([O-])[O-].[K+].[K+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CN(C=O)C>[C:13]1([CH2:12][O:4][C:1](=[O:5])[C:2]#[CH:3])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10110Propiolic AcidHCID 11430Potassium Carbonate

Product 1

HCID 543064Benzyl propiolateYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of propiolic acid (1.79 mL (2.04 g), 28.65 mmol) and potassium carbonate (4.87 g, 35.2 mmol) in anhydrous DMF (40 mL) was added benzyl bromide (3.78 mL (5.43 g of 99% pure), 31.4 mmol). The reaction mixture was stirred at room temperature for 16 h. The resulting heterogeneous mixture was poured into 40 mL of H2O and was extracted with ethyl ether (3×40 mL). The combined ether extracts were dried (Na2SO4). Filtration and concentration provided 12.16 g of crude product, which upon high vacuum distillation yielded 2-propynoic acid phenylmethyl ester (bp 60° C. 0.5 mm) as a clear oil (3.57 g, 22.3 mmol) in 78% yield.

Workup

  1. extractionwas extracted with ethyl ether (3×40 mL)
  2. dry with materialThe combined ether extracts were dried (Na2SO4)
  3. filtrationFiltration and concentration
  4. customprovided 12.16 g of crude product, which
  5. distillationupon high vacuum distillation

Sources & evidence

ORD record
ord-b94b9dea788d4446bd4ee696fbc68d6e
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

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