Ethanol → Ethyl 2-[4-(2-methylpropyl)phenyl]propanoate

HRID 1870830Notes

Reaction equation

HRID 1870830 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[C:12]([O:14][CH2:21][CH3:22])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 3672Ibuprofen, (+-)-

Product 1

HCID 170486Ethyl 2-[4-(2-methylpropyl)phenyl]propanoate

Procedure

Under a nitrogen atmosphere, 2-(4-isobutylphenyl)-propionic acid (15.0 g) was dissolved in ethanol (200 ml), and conc. sulfuric acid (1 ml) was added, after which the solution was stirred with heating under reflux for 15 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, diluted with ethyl acetate, and thereafter neutralized with a saturated aqueous sodium bicarbonate solution. After extraction with ethyl acetate, the organic layer was dried over sodium sulfate and then concentrated under reduced pressure to obtain ethyl 2-(4-isobutyl-phenyl)-propionate.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 15 hours
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with ethyl acetate
  5. extractionAfter extraction with ethyl acetate
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-452ebfc58bf84a5c953797ffbddbe9df
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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