2-Methoxyethanol → p-Isobutylphenylacetic acid-2-methoxyethyl ester

HRID 26460Notes

Reaction equation

HRID 26460 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](Cl)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:22][O:23][CH2:24][CH2:25][OH:26]>>[CH3:22][O:23][CH2:24][CH2:25][O:26][C:12](=[O:13])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 8471TriethylamineHCID 124225774-(2-Methylpropyl)benzeneacetyl chloride

Product 1

HCID 21323304p-Isobutylphenylacetic acid-2-methoxyethyl esterYield 67.3%

Procedure

To a solution of 3.5 g of p-isobutylphenylacetic acid chloride in 5.9 g of 2-methoxyethanol was added 1.6 g of triethylamine, and the mixture was stirred at room temperature for 4 hours. After the reaction was complete, an inorganic substance produced was filtered off. The filtrate was extracted with ether, and the extract was washed, dehydrated and applied over a column of silica gel. The adsorbates was eluted with ether, and the eluates were freed of ether to give an oily product. Distillation of the product in vacuo gave 2.8 g of p-isobutylphenylacetic acid-2-methoxyethyl ester as a colorless oil, boiling at 97°-98° C./1 mmHg. Analysis-Calculated for C15H22O3 : C, 71.97; H, 8.86. Found: C, 71.63; H, 8.90. Mass spectrum: parent ion 250 m/e.

Workup

  1. customan inorganic substance produced
  2. filtrationwas filtered off
  3. extractionThe filtrate was extracted with ether
  4. washthe extract was washed
  5. washThe adsorbates was eluted with ether
  6. customto give an oily product
  7. distillationDistillation of the product in vacuo

Sources & evidence

ORD record
ord-cdff8a6591294437abaa530021a53d05
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Reaction notes

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