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

Sigma-Aldrich

Methanol solution, contains 0.50 % (v/v) triethylamine

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Methanol solution, NMR reference standard, 4% in methanol-d₄ (99.8 atom % D), NMR tube size 3 mm × 8 in.

Supelco

1-Octanol, analytical standard

Supelco

2-Ethyl-1-hexanol, analytical standard

Sigma-Aldrich

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Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

Methanol, Pharmaceutical Secondary Standard; Certified Reference Material

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Methanol, ACS spectrophotometric grade, ≥99.9%

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1-Octanol, ReagentPlus^®, 99%

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Methanol, Laboratory Reagent, ≥99.6%

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Methanol, ACS reagent, ≥99.8%

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Methanol, anhydrous, ≥99.5%

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Methanol, LR, ≥99%

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Methanol, AR, ≥99.5%

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Methanol, suitable for HPLC, ≥99.9%

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Methanol, BioReagent, ≥99.93%

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Methanol, suitable for HPLC, gradient grade, ≥99.9%

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USP

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Toluene, ACS reagent, ≥99.5%

Sigma-Aldrich

Toluene, ACS reagent, ≥99.5%

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Toluene, LR, ≥99%

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Toluene, AR, ≥99.5%

Supelco

Residual Solvent - Toluene, Pharmaceutical Secondary Standard; Certified Reference Material

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Toluene, suitable for HPLC, ≥99.8%

Sigma-Aldrich

Toluene, Laboratory Reagent, ≥99.3%

Sigma-Aldrich

Toluene, ACS reagent, ≥99.5%

Sigma-Aldrich

Toluene, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.7% (GC)