Water → 2-(4-Isobutylphenyl)propionic acid-m-fluorobenzyl ester

HRID 26456

Reaction equation

HRID 26456 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].[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][OH:21].C(N(CC)CC)C.O>O1CCCC1>[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][O:21][C:12](=[O:13])[CH:11]([C:8]1[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 680083-Fluorobenzylic alcoholHCID 595157alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

Product 1

HCID 213233132-(4-Isobutylphenyl)propionic acid-m-fluorobenzyl esterYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.4 g of 2-(4-isobutylphenyl)propionic acid chloride and 3.7 g of m-fluorobenzyl alcohol in 30 ml of tetrahydrofuran was added 3.7 g of triethylamine, dropwise under cooling, and the mixture was reacted at room temperature for 1.5 hours. After the reaction was complete, the crystals procuced 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. The ether extract was dehydrated and freed of ether by distillation. The oily residue thus obtained was distilled in vacuo to yield 5.9 g of 2-(4-isobutylphenyl)propionic acid-m-fluorobenzyl ester as a colorless oil, boiling at 143°-144° C./0.2 mmHg. Mass spectrum: parent ion 314 m/e.

Workup

  1. temperaturedropwise under cooling
  2. customthe mixture was reacted at room temperature for 1.5 hours
  3. customthe crystals procuced were removed by filtration
  4. distillationThe filtrate was freed of solvent by distillation
  5. customto leave a residue
  6. extractionThe resulting mixture was extracted with ether
  7. extractionThe ether extract
  8. distillationfreed of ether by distillation
  9. customThe oily residue thus obtained
  10. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-e9f0690edfb64c1b8140ef79b651e53a
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Linked notes

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