Ethyl 3-bromopropionate → 2-Pentylglutaric acid

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Reaction Steps

A solution of 29.4 g of 4-hydroxymethyl-1-p-ethoxyphenyl-1-nonanol [obtainable by reaction of diethyl 2-pentylmalonate (boiling point 127°/13 mbar) with ethyl 3-bromopropionate to give diethyl 2-carboethoxy-2-pentylglutarate (boiling point 160°/0.4 mbar), hydrolysis and decarboxylation to give 2-pentylglutaric acid, heating to form the anhydride (boiling point 120°/0.7 mbar), reaction with phenetol/AlCl3 to give 4-p-ethoxybenzoyl-2-pentylbutyric acid (m.p. 61°) and reduction with LiAlH4 ] and 1 g of p-toluenesulfonic acid in 400 ml of benzene is boiled under a water separator for 6 hours, then the mixture is washed with NaHCO3 solution, dried, evaporated and 2-p-ethoxyphenyl-5-pentyltetrahydropyran is obtained.

Provenance & Evidence