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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

Supelco

2,6-Pyridinedicarboxylic acid concentrate, 0.02 M C₇H₅NO₄ in water (0.04N), suitable for ion chromatography, eluent concentrate

Sigma-Aldrich

2-Ethyl-1-hexanol, ≥99.6%

Sigma-Aldrich

3-Phenyl-1-propanol, ≥98%, FCC

Supelco

Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Isopropyl alcohol, ≥99.7%, FCC, FG

Sigma-Aldrich

1-Octanol, anhydrous, ≥99%

Supelco

1-Octanol, analytical standard

Sigma-Aldrich

2-Ethyl-1-hexanol, puriss., ≥99.0% (GC)

Sigma-Aldrich

3-Phenyl-1-propanol, 98%

Sigma-Aldrich

Methanol, purification grade, 99.8%

Sigma-Aldrich

Methanol, ACS spectrophotometric grade, ≥99.9%

Supelco

2-Ethyl-1-hexanol, analytical standard

Sigma-Aldrich

Methanol, BioReagent, ≥99.93%

Sigma-Aldrich

Ethyl alcohol, Pure 190 proof, for molecular biology

Sigma-Aldrich

Methanol, puriss., meets analytical specification of Ph Eur, ≥99.7% (GC)

Sigma-Aldrich

2,6-Pyridinedicarboxylic acid, 99%

Sigma-Aldrich

Methanol, anhydrous, 99.8%

Sigma-Aldrich

1-Octanol, ≥98%, FCC, FG

Sigma-Aldrich

1-Octanol, natural, ≥98%, FCC

Supelco

2,6-Pyridinedicarboxylic acid, suitable for ion chromatography, ≥99.5% (T)

Supelco

Ethanol standards 10% (v/v), 10 % (v/v) in H₂O, analytical standard

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2-Ethyl-1-hexanol, ≥99%, FG

Supelco

Ethanol solution, certified reference material, 2000 μg/mL in methanol

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Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Methanol, suitable for HPLC, gradient grade, suitable as ACS-grade LC reagent, ≥99.9%

Sigma-Aldrich

1-Octanol, suitable for HPLC, ≥99%

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Ethanol Fixative 80% v/v, suitable for fixing solution (blood films)

Sigma-Aldrich

Methanol, suitable for HPLC, ≥99.9%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Methanol, Laboratory Reagent, ≥99.6%