C[Si](C)(C)C1C=C(Br)C=C([Si](C)(C)C)C=1.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=O)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].S(Cl)([Cl:33])=O>CN(C)C=O.C(Cl)Cl.C(C1C=CC(CCC(O)=O)=CC=1)(C)(C)C>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([Cl:33])=[O:30])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]A 2 L 3 neck round bottom flask fit with a condenser, thermometer, nitrogen inlet, and overhead stirrer was charged with 3-(4-t-butylphenyl)propionic acid (118.7 g, 0.576 mol),thionyl chloride (210 mL, 2.88 mol), dimethylformamide (3 drops), and methylene chloride solvent. The reaction was refluxed for 3 hours and additional 3-(4-t-butylphenyl)propionic acid (8.17 g, 0.040 mol) was added to the reactor and refluxed for an additional hour. After allowing to stand overnight, the reaction was stripped of volatiles to yield the crude 3-(4-t-butylphenyl)propionyl chloride (99.0 g). 1HNMR (CDCl3, 500 MHz) δ7.33 (d, JAB=8 Hz, 2H); 7.12 (d, JAB=8 Hz, 2H); 3.20 (t, J=7.5 Hz, 2H); 2.98 (t, J=7.5, 2H); 1.31 (s, 9H).
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