Br[CH:2]([CH3:6])[C:3]([O-:5])=[O:4].[Na+].[CH2:8]([C:12]1[CH:17]=[CH:16][C:15]([Mg]Br)=[CH:14][CH:13]=1)[CH:9]([CH3:11])[CH3:10].O.S(=O)(=O)(O)O>C1COCC1>[CH2:8]([C:12]1[CH:17]=[CH:16][C:15]([CH:2]([CH3:6])[C:3]([OH:5])=[O:4])=[CH:14][CH:13]=1)[CH:9]([CH3:11])[CH3:10]A suspension of 1.75 g of sodium α-bromopropionate in 20 ml of THF was added to 15 ml of a 0.67 M solution of p-isobutylphenyl magnesium bromide in THF. The mixture was heated under reflux for 1 hour, and then cooled. Then, 15 ml of water and then 5 ml of 20% sulfuric acid were added. The mixture was stirred for 10 to 15 minutes, and extracted with diethyl ether. The extract was washed with water, and then, extracted with a 1 N aqueous solution of potassium carbonate. The extract was washed with diethyl ether. The resulting aqueous layer was added to a mixture of 10 ml of concentrated hydrochloric acid and 20 ml of water, and the mixture was extracted with diethyl ether. The extract was washed with water, dried, concentrated and purified by silica gel column chromatography to give 0.21 g (yield 10.2%) of α-(p-isobutylphenyl)propionic acid.
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