Ethanol → HCID 11775728, compound

HRID 1360212Notes

Reaction equation

HRID 1360212 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:20][CH3:21])=[O:13])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 782804-(4-Methoxyphenyl)butyric acid

Product 1

HCID 11775728HCID 11775728, compound

Procedure

After 4-(4-methoxyphenyl)butanoic acid (200 g) and then concentrated sulfuric acid (4 ml) were added to ethanol (400 ml), the resulting mixture was heated under reflux for 1 hour. About one-half of the solvent was distilled off under reduced pressure, and the residual reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate (1 L). The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain ethyl 4-(4-methoxyphenyl)butanoate quantitatively.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. distillationAbout one-half of the solvent was distilled off under reduced pressure
  4. additionthe residual reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution
  5. extractionextracted with ethyl acetate (1 L)
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e83e6ae555e74052908693b46bef9440
Source dataset
uspto-grants-2011_02
Patent number
US07879843B2

Reaction notes

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