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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
Benzyl alcohol, natural, ≥98%, FG
Sigma-Aldrich
Benzyl alcohol, anhydrous, 99.8%
Sigma-Aldrich
TEMPO, 98%
Sigma-Aldrich
Benzyl alcohol, ≥99%, FCC, FG
Sigma-Aldrich
Phenethyl alcohol, natural, ≥99%, FCC, FG
Sigma-Aldrich
Phenethyl alcohol, ≥99%, FCC, FG
Sigma-Aldrich
Tetrabutylammonium bromide, ACS reagent, ≥98.0%
Sigma-Aldrich
TEMPO, purified by sublimation, 99%
Supelco
Benzyl alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
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
2-Propanol, anhydrous, 99.5%
Sigma-Aldrich
Toluene, anhydrous, 99.8%
Sigma-Aldrich
Toluene, ACS reagent, ≥99.5%
Sigma-Aldrich
2-Propanol, ACS reagent, ≥99.5%
Sigma-Aldrich
Isopropyl alcohol, meets USP testing specifications
Sigma-Aldrich
Benzyl alcohol, puriss. p.a., ACS reagent, ≥99.0% (GC)
Sigma-Aldrich
2-Propanol, Laboratory Reagent, ≥99.5%
Sigma-Aldrich
Toluene, Laboratory Reagent, ≥99.3%
Sigma-Aldrich
2-Propanol, ACS reagent, ≥99.5%
Sigma-Aldrich
Toluene, ACS reagent, ≥99.5%
Sigma-Aldrich
Benzyl alcohol, puriss., meets analytical specification of Ph. Eur., BP, NF, 99-100.5% (GC)
Sigma-Aldrich
Ethanol, puriss. p.a., absolute, ≥99.8% (GC)
Benzyl alcohol, European Pharmacopoeia (EP) Reference Standard
USP
Benzyl alcohol, United States Pharmacopeia (USP) Reference Standard
Supelco
Toluene, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
Methanol solution, contains 0.10 % (v/v) formic acid, UHPLC, suitable for mass spectrometry (MS), ≥99.5%