1-Bromopentane → 2-Pentylbutanedioic acid

Participants

Reaction Steps

A method similar to that described by Devlin, et al, J. Chem. Soc., Perkin Transactions I, page 830 (1975) was used. Sodium ethoxide was formed by the addition of sodium metal (2.25 g, 91.59 mmol) to anhydrous EtOH (150 ml) under an N2 atmosphere. To the resultant solution was added triethyl-1,1,2-ethanetricaboxylate (obtained from Aldrich; 21 ml, 91.59 mmol) followed by dropwise addition of n-pentyl bromide (11.4 ml, 91.59 mmol). The mixture was brought to reflux and stirred overnight (19 hr). After the reaction had cooled, it was filtered and concentrated. The residue was treated with H2O and extracted with Et2O (three times). The combined organic extracts were dried (MgSO4), concentrated and purified by vacuum distillation (85° C./22.66 Pascals) to yield a colorless liquid (26.37 g, 91% yield).

Provenance & Evidence