1-Propanol → Propyl 2-[4-(2-methylpropyl)phenyl]propanoate

HRID 26458

Reaction equation

HRID 26458 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)[CH2:22][CH3:23]>>[CH2:21]([O:13][C:12](=[O:14])[CH:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=1)[CH3:15])[CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 3672Ibuprofen, (+-)-

Product 1

HCID 9837805Propyl 2-[4-(2-methylpropyl)phenyl]propanoateYield 89.7%

Procedure

A mixture of 5 g of 2-(4-isobutylphenyl)propionic acid, 7.3 g of n-propyl alcohol and 7.1 g of sulfuric acid was refluxed for 6 hours. After cooling, to the mixture was added ice-water. The resulting mixture was extracted with ether, and the extract was dehydrated. The ether was removed by distillation from the extract to leave an oily product. This product was distilled in vacuo to give 5.4 g of 2-(4-isobutylphenyl)propionic acid-n-propyl ester as a colorless oil, boiling at 100°-103° C./0.3 mmHg. Mass spectrum: parent ion 248 m/e.

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperatureAfter cooling, to the mixture
  3. extractionThe resulting mixture was extracted with ether
  4. customThe ether was removed by distillation from the
  5. extractionextract
  6. customto leave an oily product
  7. distillationThis product was distilled in vacuo

Sources & evidence

ORD record
ord-17288f7d2b224ce2b8902e103c5a74e6
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Linked notes

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