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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

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

Sigma-Aldrich

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

Sigma-Aldrich

2,6-Pyridinedicarboxylic acid, 99%

Sigma-Aldrich

3-Phenyl-1-propanol, ≥98%, FCC

Sigma-Aldrich

2-Ethyl-1-hexanol, ≥99.6%

Supelco

2-Ethyl-1-hexanol, analytical standard

Sigma-Aldrich

3-Phenyl-1-propanol, 98%

Sigma-Aldrich

2-Ethyl-1-hexanol, ≥99%, FG

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1-Octanol, natural, ≥98%, FCC

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Isopropyl alcohol, ≥99.7%, FCC, FG

Sigma-Aldrich

1-Octanol, ≥98%, FCC, FG

Supelco

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

Supelco

1-Octanol, analytical standard

Sigma-Aldrich

1-Octanol, anhydrous, ≥99%

Supelco

Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

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

Sigma-Aldrich

Methanol, HPLC Plus, ≥99.9%

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

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

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Methanol, anhydrous, 99.8%

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Methanol, suitable for HPLC, ≥99.9%

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Methanol, BioReagent, ≥99.93%

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Methanol, Laboratory Reagent, ≥99.6%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Supelco

Methanol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

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

Sigma-Aldrich

Methanol, ACS spectrophotometric grade, ≥99.9%