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Efficient and simple approaches towards direct oxidative esterification of alcohols.

Efficient and simple approaches towards direct oxidative esterification of alcohols.

Chemistry (Weinheim an der Bergstrasse, Germany) (2014-10-07)

Ritwika Ray, Rahul Dev Jana, Mayukh Bhadra, Debabrata Maiti, Goutam Kumar Lahiri

ABSTRACT

The present article describes novel oxidative protocols for direct esterification of alcohols. The protocols involve successful demonstrations of both "cross" and "self" esterification of a wide variety of alcohols. The cross-esterification proceeds under a simple transition-metal-free condition, containing catalytic amounts of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy)/TBAB (tetra-n-butylammonium bromide) in combination with oxone (potassium peroxo monosulfate) as the oxidant, whereas the self-esterification is achieved through simple induction of Fe(OAc)2 /dipic (dipic=2,6-pyridinedicarboxylic acid) as the active catalyst under an identical oxidizing environment.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Benzyl alcohol, anhydrous, 99.8%

Sigma-Aldrich

TEMPO, 98%

Sigma-Aldrich

TEMPO, purified by sublimation, 99%

Sigma-Aldrich

Toluene, suitable for HPLC, ≥99.9%

Supelco

Methanol solution, contains 0.10 % (v/v) formic acid, UHPLC, suitable for mass spectrometry (MS), ≥99.5%

Supelco

Phenylethyl Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

Benzyl alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Toluene, anhydrous, 99.8%

Supelco

Benzyl alcohol, analytical standard

Sigma-Aldrich

Cyclohexanol, ReagentPlus^®, 99%

Sigma-Aldrich

2-Phenylethanol, ≥99.0% (GC)

Sigma-Aldrich

Phenethyl alcohol, ≥99%, FCC, FG

Sigma-Aldrich

Tetrabutylammonium bromide solution, 50 wt. % in H₂O

Sigma-Aldrich

Benzyl alcohol, ≥99%, FCC, FG

Sigma-Aldrich

Phenethyl alcohol, natural, ≥99%, FCC, FG

Supelco

Toluene, analytical standard

Sigma-Aldrich

Benzyl alcohol, natural, ≥98%, FG

Supelco

Toluene, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

2-Propanol, electronic grade, 99.999% trace metals basis

Sigma-Aldrich

2-Propanol, HPLC Plus, for HPLC, GC, and residue analysis, 99.9%, poly coated bottles

Sigma-Aldrich

Tetrabutylammonium bromide, ReagentPlus^®, ≥99.0%

Sigma-Aldrich

2-Propanol, BioReagent, ≥99.5%, Molecular Biology

Supelco

2-Propanol, analytical standard

Sigma-Aldrich

2-Propanol, BioUltra, Molecular Biology, ≥99.5% (GC)

Sigma-Aldrich

2-Propanol, ACS reagent, ≥99.5%

Sigma-Aldrich

2-Propanol, anhydrous, 99.5%

Sigma-Aldrich

Tetrabutylammonium bromide, ACS reagent, ≥98.0%

Supelco

Tetrabutylammonium bromide, suitable for ion pair chromatography, LiChropur^™, ≥99.0%

USP

2-Propanol, United States Pharmacopeia (USP) Reference Standard

Sigma-Aldrich

2-Propanol, suitable for HPLC, 99.5%