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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

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

Sigma-Aldrich

Methanol, anhydrous, 99.8%

Supelco

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

Sigma-Aldrich

1-Octanol, natural, ≥98%, FCC

Sigma-Aldrich

Isopropyl alcohol, ≥99.7%, FCC, FG

Sigma-Aldrich

1-Octanol, anhydrous, ≥99%

Sigma-Aldrich

1-Octanol, ≥98%, FCC, FG

Supelco

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

Sigma-Aldrich

2-Ethyl-1-hexanol, ≥99%, FG

Sigma-Aldrich

2,6-Pyridinedicarboxylic acid, 99%

Sigma-Aldrich

3-Phenyl-1-propanol, 98%

Sigma-Aldrich

2-Ethyl-1-hexanol, ≥99.6%

Sigma-Aldrich

Methanol, SAJ first grade, ≥99.5%

Sigma-Aldrich

1-Octanol, SAJ first grade, ≥75.0%

Sigma-Aldrich

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

Sigma-Aldrich

Methanol, JIS special grade, ≥99.8%

Supelco

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

Sigma-Aldrich

Ethanol, JIS first grade, 94.8-95.8%

Sigma-Aldrich

Methanol, suitable for HPLC, gradient grade, 99.93%

Sigma-Aldrich

3-Phenyl-1-propanol, ≥98%, FCC

Sigma-Aldrich

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

Supelco

Toluene, analytical standard

Sigma-Aldrich

Toluene, anhydrous, 99.8%

Supelco

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

Supelco

Toluene, HPLC grade, 99.8%

Supelco

1-Octanol, analytical standard

Supelco

Methanol, analytical standard

Supelco

2-Ethyl-1-hexanol, analytical standard

Sigma-Aldrich

1-Octanol, JIS special grade, ≥98.0%

Sigma-Aldrich

Ethanol, JIS special grade, 94.8-95.8%