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

HRID 346044Notes

Reaction equation

HRID 346044 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 Na 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-b6c64f0425c24371b5499094e9467e57
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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