Convenient Large-Scale Synthesis of d-Glucaro-1,4:6,3-dilactone

Calcium d-glucarate was converted into d-glucaro-1,4:6,3-dilactone on 32-g, 1-kg, and 22-kg scale, using azeotropic distillation with methyl isobutyl ketone to drive the dehydration. The crystalline product was ≥99.5% pure by GC and NMR, and overall yield was as high as 72%.

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2009-11, Vol.74 (21), p.8373-8376
Main Authors: Gehret, Troy C, Frobese, A. Stephen, Zerbe, James S, Chenault, H. Keith
Format: Article
Language:English
Subjects:
Chemistry
Crystallization
Exact sciences and technology
Glucaric Acid - analogs & derivatives
Glucaric Acid - chemical synthesis
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lactones - chemical synthesis
Magnetic Resonance Spectroscopy
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Calcium d-glucarate was converted into d-glucaro-1,4:6,3-dilactone on 32-g, 1-kg, and 22-kg scale, using azeotropic distillation with methyl isobutyl ketone to drive the dehydration. The crystalline product was ≥99.5% pure by GC and NMR, and overall yield was as high as 72%.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9015985