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Updated: Jul 30, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
rac-N-(4-Eth-oxy-phen-yl)-3-hy-droxy-butanamide
James E Hines Iii1, Zechariah Myles1, Garrick Breaux1
1Department of Environmental Toxicology, Southern University and A&M College, Baton Rouge, LA 70813, USA.
Abstract:
In the title compound, racemic bucetin [systematic name: N-(4-eth-oxy-phen-yl)-3-hydroxy-butanamide], C12H17NO3, the mol-ecule is in an extended conformation as illustrated by the C-O-C-C torsion angle [170.14 (15)°] in the eth-oxy group and the subsequent C-N-C-C [-177.24 (16)°], N-C-C-C [170.08 (15)°] and C-C-C-C [171.41 (15)°] torsion angles in the butanamide chain. In the crystal, the O-H group donates an inter-molecular O-H⋯O hydrogen bond to the amide carbonyl oxygen atom and also accepts an inter-molecular N-H⋯O hydrogen bond from an adjacent N-H group. The former forms 12-membered dimeric rings about inversion centers, and the latter form chains in the [001] direction. The overall hydrogen-bonded network is two-dimensional, with no propagation in the [100] direction.
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