Skip to Content

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

2-Propanol, Laboratory Reagent, ≥99.5%

Sigma-Aldrich

2-Propanol, anhydrous, 99.5%

Supelco

Benzyl alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

Phenylethyl Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Ethyl alcohol, Pure, 190 proof, ACS spectrophotometric grade, 95.0%

USP

Benzyl alcohol, United States Pharmacopeia (USP) Reference Standard

Benzyl alcohol, European Pharmacopoeia (EP) Reference Standard

USP

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

Sigma-Aldrich

2-Propanol, ACS reagent, ≥99.5%

Sigma-Aldrich

TEMPO, 98%

Sigma-Aldrich

TEMPO, purified by sublimation, 99%

Sigma-Aldrich

Methanol solution, suitable for NMR (reference standard), 4% in methanol-d₄ (99.8 atom % D), NMR tube size 3 mm × 8 in.

Sigma-Aldrich

Ethanol, purum, secunda spirit, denaturated with 2% 2-butanone, S15, ~96% (based on denaturant-free substance)

Sigma-Aldrich

Ethanol, tested according to Ph. Eur.

Sigma-Aldrich

Ethyl alcohol, Pure, 200 proof, ACS reagent, ≥99.5%

Sigma-Aldrich

2-Propanol, suitable for HPLC, 99.5%

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

Isopropyl alcohol, meets USP testing specifications

Sigma-Aldrich

2-Propanol, puriss. p.a., ACS reagent, ≥99.8% (GC)

Sigma-Aldrich

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

Sigma-Aldrich

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

Supelco

2-Propanol, analytical standard

Sigma-Aldrich

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

Supelco

2-Propanol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

2-Propanol, suitable for HPLC, 99.9%

Sigma-Aldrich

2-Phenylethanol, ≥99.0% (GC)

Sigma-Aldrich

Benzyl alcohol, anhydrous, 99.8%

Sigma-Aldrich

Benzyl alcohol, ReagentPlus^®, ≥99%

Supelco

Benzyl alcohol, analytical standard