Gamma-Butyrolactone → 4-(4-methoxyphenoxy)butanoic acid

HRID 610389Notes

Reaction equation

HRID 610389 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.CC[O-].[Na+].[C:14]1(=[O:19])[O:18][CH2:17][CH2:16][CH2:15]1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:17][CH2:16][CH2:15][C:14]([OH:19])=[O:18])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7302Gamma-ButyrolactoneHCID 90154-MethoxyphenolHCID 2723922Sodium ethoxide

Product 1

HCID 2496494-(4-methoxyphenoxy)butanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
155 °C

Procedure

4-Methoxyphenol was added to a solution of NaOC2H5 made by dissolving 2.3 g of Ka in 50 ml ethanol. After 5 minutes, gamma-butyrolactone was added and the mixture heated at reflux overnight. Ethanol was distilled off and the residue heated at 155° C. overnight, then cooled, diluted with water and acidified to pH 3 with dilute hydrochloric acid. The product was collected by filtration, 19.5 g, m.p. 103-104° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. distillationEthanol was distilled off
  4. temperaturecooled
  5. additiondiluted with water
  6. filtrationThe product was collected by filtration, 19.5 g, m.p. 103-104° C.

Sources & evidence

ORD record
ord-c19334e6556e4c52bfd69ba97c29e7a3
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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