2-Methoxyethanol → p-Isobutylphenylacetic acid-2-methoxyethyl ester
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]=1Participants
4
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.