Heptylbenzene → HCID 22420397, compound

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Reaction Steps

First, 3,3-dimethylglutaric anhydride (25 g, 0.176 moles) is heated with 1-phenylheptane (150 ml) and anhydrous aluminium chloride (51.6 g, 0.387 moles) at 90°-100° C. for 1 hour. The reaction mixture is cooled to room temperature, poured into a mixture of ice water (500 ml) and concentrated hydrochloric acid (100 ml), and extracted with ether (3×150). The combined ether extracts are dried over anhydrous magnesium sulfate and filtered. Ether is removed under reduced pressure and the resulting solution chromatographed on silica gel (hexane and then hexane:ether:acetic acid at 80:20:1) to yield 4-(4-heptylbenzoyl)-3,3-dimethyl butanoic acid (17.67 g), m.p. 41°-42° C.

Provenance & Evidence