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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-Propanol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Toluene, SAJ first grade, ≥99.0%

Sigma-Aldrich

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

Sigma-Aldrich

Benzyl alcohol, SAJ special grade, ≥99.0%

Sigma-Aldrich

Ethanol, JIS special grade, ≥99.5%

Sigma-Aldrich

Ethanol, ≥99.5%

Sigma-Aldrich

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

Sigma-Aldrich

Toluene, JIS 1000, for residue analysis, ≥99.8%

Sigma-Aldrich

Ethanol, ≥99.5%, suitable for fluorescence

Sigma-Aldrich

2-Propanol, JIS special grade, ≥99.5%

Sigma-Aldrich

Toluene, JIS special grade, ≥99.5%

Sigma-Aldrich

Ethanol, ≥99.5%, SAJ super special grade

Sigma-Aldrich

Ethanol, SAJ first grade, ≥99.5%

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

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Cyclohexanol, SAJ first grade, ≥95.0%

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Methanol-¹²C, 99.95 atom % ¹²C

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2-Propanol, suitable for HPLC

Sigma-Aldrich

2-Propanol, SAJ first grade, ≥99.0%

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

Supelco

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2-Propanol, analytical standard

Supelco

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Sigma-Aldrich

2-Propanol, BioUltra, for molecular biology, ≥99.5% (GC)

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2-Propanol, BioReagent, for molecular biology, ≥99.5%

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TEMPO, 98%

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Tetrabutylammonium bromide, ACS reagent, ≥98.0%

Sigma-Aldrich

TEMPO, purified by sublimation, 99%

Sigma-Aldrich

Phenethyl alcohol, ≥99%, FCC, FG

Sigma-Aldrich

2-Phenylethanol, ≥99.0% (GC)

Supelco

Toluene, Pharmaceutical Secondary Standard; Certified Reference Material