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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

Ethyl alcohol, Pure, 190 proof, ACS spectrophotometric grade, 95.0%

Sigma-Aldrich

Toluene, anhydrous, 99.8%

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Ethyl alcohol, Pure, 190 proof, meets USP testing specifications

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2-Propanol, anhydrous, 99.5%

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2-Propanol, 99.5%, HPLC grade

Supelco

Toluene, HPLC grade, 99.8%

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Methanol-¹²C, 99.95 atom % ¹²C

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2-Propanol, HPLC Plus, for HPLC, GC, and residue analysis, 99.9%, poly coated bottles

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2-Propanol, ACS reagent, ≥99.5%

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Toluene, JIS 300, for residue analysis, ≥99.8%

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Cyclohexanol, JIS special grade, ≥98.0%

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2-Propanol, SAJ first grade, ≥99.0%

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2-Propanol, JIS special grade, ≥99.5%

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Ethanol, JIS 300, ≥99.5%, for residue analysis

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Toluene, SAJ first grade, ≥99.0%

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Ethanol, JIS 1000, ≥99.5%, for residue analysis

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Ethanol, ≥99.5%, suitable for absorption spectrum analysis

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2-Propanol, suitable for HPLC

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Ethanol, ≥99.5%, suitable for HPLC

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Toluene, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%

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2-Propanol, ACS reagent, ≥99.5%

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Sigma-Aldrich

Benzyl alcohol, puriss., meets analytical specification of Ph. Eur., BP, NF, 99-100.5% (GC)