Water → 2-(4-Isobutylphenyl)propionic acid-p-methylbenzyl ester

HRID 26457

Reaction equation

HRID 26457 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12](Cl)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=1.CN(C)C.O>O1CCCC1>[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:22][C:12](=[O:13])[CH:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=2)[CH3:15])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1146TrimethylamineHCID 115054-Methylbenzyl alcoholHCID 595157alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

Product 1

HCID 130346022-(4-Isobutylphenyl)propionic acid-p-methylbenzyl esterYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.4 g of 2-(4-isobutylphenyl)propionic acid chloride and 3.5 g of p-methylbenzyl alcohol in 30 ml of tetrahydrofuran was added 3.7 g of trimethylamine, dropwise under cooling, and reacted at room temperature for 2 hours. After the reaction was complete, the crystals produced were removed by filtration. The filtrate was freed of solvent by distillation to leave a residue, to which was added water. The resulting mixture was extracted with ether, and the extract was dehydrated and freed of solvent by distillation to give an oily residue. This residue was then distilled in vacuo to yield 6.3 g of 2-(4-isobutylphenyl)propionic acid-p-methylbenzyl ester as a colorless oil, boiling at 139°-140° C./0.1 mmHg. Mass spectrum: parent ion 310 m/e.

Workup

  1. temperaturedropwise under cooling
  2. customreacted at room temperature for 2 hours
  3. customthe crystals produced
  4. customwere removed by filtration
  5. distillationThe filtrate was freed of solvent by distillation
  6. customto leave a residue
  7. extractionThe resulting mixture was extracted with ether
  8. distillationfreed of solvent by distillation
  9. customto give an oily residue
  10. distillationThis residue was then distilled in vacuo

Sources & evidence

ORD record
ord-27b731b27ea44fdfacc7ad82e600c1a0
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Linked notes

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