Ethanol → 4-Pentynoic acid ethyl ester

HRID 1189062Notes

Reaction equation

HRID 1189062 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].OS(O)(=O)=O.[CH2:13](O)[CH3:14]>>[C:1]([O:7][CH2:13][CH3:14])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 224644-Pentynoic acid

Product 1

HCID 1439504-Pentynoic acid ethyl esterYield 70%

Conditions

Temperature
50 °C

Procedure

In analogy to the method as described in Tetrahedron., 2000, 56, 5735-5742, a mixture of the 4-pentynoic acid (10 g, 102 mmol) and H2SO4 98% (0.338 mL, 6.12 mmol) in ethanol (113 mL) was heated at 50° C. overnight. The reaction mixture was concentrated and the crude product was dissolved in ethyl acetate, washed with NaHCO3 1M and water. The solvent was removed under reduced pressure to afford 9.04 g of ethyl pent-4-ynoate (Yield: 70%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe crude product was dissolved in ethyl acetate
  3. washwashed with NaHCO3 1M and water
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d362a98e4d7c48d38543ea478b1af407
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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