Methanol → Nonanoic acid, 9-hydroxy-, methyl ester

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Reaction Steps

Azelaic acid monomethyl ester (20 mmole) was dissolved in tetrahydrofuran (100 mL) and kept in argon atmosphere at −10° C. Trietbylamine (30 mmole) was added dropwise to the reaction flask, followed by the addition of ethyl chloroformate (25 mmole). The solution was stirred for 20 minutes, and sodium borohydride (60 mmole) was added in one portion. Methanol (40 mL) was added dropwise and the reaction flask was kept at 0° C. for 40 minutes. Water (20 mL) was added and organic solvent was removed by rotavap. The residue was brought to water and ethyl acetate for partition. The organic layer was collected and dried to obtain 9-hydroxy-nonanoic acid methyl ester in decent purity for use in Step 4. The yield is >90%.

Provenance & Evidence