Skip to Content
Merck
  • 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
TEMPO, purified by sublimation, 99%
Supelco
2-Propanol, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
Benzyl alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
Phenylethyl Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Ethanol, for residue analysis
Sigma-Aldrich
2-Propanol, HPLC Plus, for HPLC, GC, and residue analysis, 99.9%, poly coated bottles
Sigma-Aldrich
Benzyl alcohol, anhydrous, 99.8%
Sigma-Aldrich
Phenethyl alcohol, ≥99%, FCC, FG
Sigma-Aldrich
Tetrabutylammonium bromide solution, 50 wt. % in H2O
Sigma-Aldrich
Ethanol, tested according to Ph. Eur.
Supelco
2-Propanol, analytical standard
Supelco
Tetrabutylammonium bromide, suitable for ion pair chromatography, LiChropur, ≥99.0%
Sigma-Aldrich
2-Phenylethanol, ≥99.0% (GC)
Sigma-Aldrich
Cyclohexanol, ReagentPlus®, 99%
Sigma-Aldrich
Toluene, anhydrous, 99.8%
Sigma-Aldrich
Benzyl alcohol, ≥99%, FCC, FG
Sigma-Aldrich
TEMPO, 98%
Sigma-Aldrich
Phenethyl alcohol, natural, ≥99%, FCC, FG
Sigma-Aldrich
Tetrabutylammonium bromide, ReagentPlus®, ≥99.0%
Sigma-Aldrich
2-Propanol, anhydrous, 99.5%
Sigma-Aldrich
Benzyl alcohol, natural, ≥98%, FG
Supelco
Toluene, analytical standard
Sigma-Aldrich
Ethanol, BioUltra, for molecular biology, ≥99.8%, (absolute alcohol, without additive, A15 o1)
Sigma-Aldrich
2-Propanol, electronic grade, 99.999% trace metals basis
Sigma-Aldrich
2-Propanol, for molecular biology, BioReagent, ≥99.5%
Sigma-Aldrich
2-Propanol, BioUltra, for molecular biology, ≥99.5% (GC)
Sigma-Aldrich
2-Propanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)
Sigma-Aldrich
Toluene, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%
Sigma-Aldrich
Tetrabutylammonium bromide, ACS reagent, ≥98.0%
Supelco
Residual Solvent - Toluene, Pharmaceutical Secondary Standard; Certified Reference Material