Pentylbenzene → 6-Oxo-6-(4-pentylphenyl)hexanoic acid

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Reaction Steps

Adipic acid monomethyl ester (35 g; 0.44 mole) is converted to the acid chloride with thionyl chloride (50 g) in a manner analogous to that described in Example 1. This product is reacted with pentylbenzene (400 ml) and aluminum chloride (80 g) and the reaction product isolated as a colorless oil (25 g; b.p. 165°-174° C. @0.15 mm) and identified as methyl 5-(4-n-pentylbenzoyl) pentanoate. This ester (5 g; 0.017 mole) is hydrolysed with sodium hydroxide in aqueous ethanol and the product isolated as in Example 1. Recrystallization from aqueous ethanol gives 5-(4-n-pentylbenzoyl)pentanoic acid (4.0 g) as colorless crystals, m.p. 84°-86° C.

Provenance & Evidence