I'm trying to react succinic anhydride with a decyl alcohol to produce mono-decyl succinate. Literature and Google searches suggest that the monoesterification should proceed without catalyst. However I'm failing to get the reactions going. Reactions were in reflux, $\pu{80-140 ^\circ C}$ at $\pu{1 atm}$.

Any suggestions if anhydride esterifications even needs a catalyst? Would a solvent help?

  • $\begingroup$ Addition of catalytic pyridine should assist it. $\endgroup$ – Waylander Feb 9 at 22:30
  • 1
    $\begingroup$ Do you use solvent? if so, what is it? Would you please include those in your question? $\endgroup$ – Mathew Mahindaratne Feb 10 at 0:46

The monoesters of succinic acid can be prepared using Steglich esterification method (Ref.1,2), which is specially suitable for alcohols with the $\ce{OH}$ functional group is in steric hindrance. In this method, dicyclohexylcarbodiimide (DCC) as the coupling reagent and 4-dimethylaminopyridine (DMAP) as a catalyst are used. The reference 1 gave a typical procedure as follows:

To a stirred solution of 10mmol carboxylic acid in $\pu{lO ml}$ anhydrous $\ce{CH2Cl2}$ (in the case of sparingly soluble acids, in DMF) is added $\pu{30-110 mg}$ DMAP and $\pu{20-40 mmol}$ alcohol or thiol ($\pu{10 mmol}$ with alcohols or thiols which are not easily removable without significant loss; $\pu{3.4 mmol}$ with glycerol). DCC is added to the reaction mixture at OT, which is then stirred for $\pu{5 min}$ at $\pu{0 ^\circ C}$ and $\pu{3 h}$ at $\pu{20 ^\circ C}$. Precipitated urea is then filtered off and the filtrate evaporated down in vacuo. The residue is taken up in $\ce{CH2Cl2}$ and, if necessary, filtered free of any further precipitated urea. The $\ce{CH2Cl2}$ solution is washed twice with $\pu{0.5 N}$ $\ce{HCl}$ and with saturated $\ce{NaHCO3}$ solution, and then dried over $\ce{MgSO4}$. The solvent is removed by evaporation and the ester isolated by distillation or recrystallization. Crystalline products can be obtained in pure form by filtration on a short silica gel column (eluent: $\ce{CH2Cl2}$ or $\ce{CHCl3}$).

For example, recently, this method has successfully used to couple Vitamin $\mathrm{D_2}$ to succinic anhydride in order to achieve succinic monoester of Vitamin $\mathrm{D_2}$ (Ref.3). However, there is an US patent publication revealing cheap solvent free method using alkali salt bases such as $\ce{NaOAc, KOAc, Na2CO3}$, and $\ce{K2CO3}$ as catalysts to efficiently prepare mono alkyl esters from cyclic anhydrides (Ref.4).


  1. Bernhard Neises, Wolfgang Steglich, "Simple Method for the Esterification of Carboxylic Acids," Angew. Chem. Int. Ed. 1978, 17(7), 522–524 (https://doi.org/10.1002/anie.197805221)(PDF).
  2. Gerhard Höfle, Wolfgang Steglich, Helmut Vorbrüggen, "4‐Dialkylaminopyridines as Highly Active Acylation Catalysts. [New synthetic method (25)]," Angew. Chem. Int. Ed. 1978, 17(8), 569-583 (https://doi.org/10.1002/anie.197805691).
  3. Victar Nyaarugwe, "Synthesis and Characterization of Hybrid Compounds for the Treatment of Bone Related Diseases," Journal of Trauma and Orthopedic Nursing 2018, 2(1:4), 16 pages (PDF).
  4. Mark, B. Erman, Joe W. Snow, Mikhail Y. Lebedev, "Process for making monomenthyl esters," US Patent 2007, US 7,247,743 B1 (PDF).

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