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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

Methanol-¹²C, 99.95 atom % ¹²C

Sigma-Aldrich

Tetrabutylammonium bromide solution, 50 wt. % in H₂O

Sigma-Aldrich

TEMPO, 98%

Sigma-Aldrich

Tetrabutylammonium bromide, ACS reagent, ≥98.0%

Sigma-Aldrich

TEMPO, purified by sublimation, 99%

Sigma-Aldrich

Ethyl alcohol, Pure, 200 proof, anhydrous, ≥99.5%

Supelco

2-Propanol, Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

2-Propanol, analytical standard

Supelco

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

Sigma-Aldrich

Toluene, anhydrous, 99.8%

Sigma-Aldrich

Ethanol, purum, absolute ethanol, denaturated with 4.8% isopropanol, A15 IPA¹, ≥99.8% (based on denaturant-free substance)

Sigma-Aldrich

Ethanol, ACS reagent, prima fine spirit, without additive, F15 o¹

Sigma-Aldrich

Isopropyl alcohol, meets USP testing specifications

Sigma-Aldrich

2-Propanol, Laboratory Reagent, ≥99.5%

Sigma-Aldrich

2-Propanol, ACS reagent, ≥99.5%

Sigma-Aldrich

Toluene, ACS reagent, ≥99.5%

Sigma-Aldrich

Methanol solution, (Methanol:Dimethyl sulfoxide 1:1 (v/v))

Sigma-Aldrich

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

Sigma-Aldrich

Ethyl alcohol, Pure, 160 proof, Excise Tax-free, Permit for use required

USP

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

Supelco

Cyclohexanol, analytical standard

Sigma-Aldrich

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

USP

Methyl alcohol, United States Pharmacopeia (USP) Reference Standard

Sigma-Aldrich

2-Propanol, suitable for HPLC, 99.9%

Sigma-Aldrich

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

Sigma-Aldrich

Ethyl alcohol, Pure, 200 proof, meets USP testing specifications

Sigma-Aldrich

2-Propanol, puriss., meets analytical specification of Ph. Eur., BP, USP, ≥99.5% (GC)

Sigma-Aldrich

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

Sigma-Aldrich

Toluene, suitable for HPLC, 99.9%

Sigma-Aldrich

2-Propanol, suitable for HPLC, 99.5%