Synthesis of dulcitol

Preparation of dulcitol

Alternative Names: Galactitol; Dulcose; Euonymit; D-Galactitol; Melampyrin;

Preparation of dulcitol

Preparation of dulcitol

10 g galactose are dissolved in 100 ml water in a stoppered bottle of about 400 ml capacity. The solution is vigorously and continuously shaken at ordinary temperature with 35 g 2.5% sodium amalgam until most of the sodium amalgam is used up. Every 15 minutes during the operation the liquid is neutralized with dilute sulfuric acid. Sodium amalgam is added again in quantities of 30 g at a time, and the shaking and neutralization is continued until 5 drops of the solution will only reduce 1 drop of Fehling’s solution. The temperature must not rise above 25° C. The operation requires about 3 hours. The quantity of good sodium amalgam required amounts to 300-400 g. The solution after having been separated from the mercury is neutralized with sulfuric acid, and is poured hot into four times its volume (about 900 ml) hot 95 % alcohol. If the filtered liquid is concentrated on the water-bath to a volume of about 20 ml, the dulcitol separates in crystalline form. After standing in ice it is filtered off and recrystallized from a little hot water. If the sodium sulfate which was precipitated by the alcohol contains any organic matter, it is boiled up with 80% alcohol, and the fitrate added to the first alcoholic solution. The yield of pure dulcitol amounts to about 5 g.

Introduction to the preparation of organic compounds, E. Fisher, 150-152, 1909

IUPAC Name

(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol

InChI

InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-

InChI Key

FBPFZTCFMRRESA-GUCUJZIJSA-N

Canonical SMILES

C(C(C(C(C(CO)O)O)O)O)O

Isomeric SMILES

C([C@H]([C@@H]([C@@H]([C@H](CO)O)O)O)O)O

MeSH Synonyms

Dulcitol, Galactitol

Depositor-Supplied Synonyms

dulcitol, galactitol, dulcose, Euonymit, D-Galactitol, Melampyrin, Melampyrit, 608-66-2, D-Dulcitol, dulcite, meso-galactitol, L-galactitol, (2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexaol, CHEBI:16813, FBPFZTCFMRRESA-GUCUJZIJSA-N, (2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol, DSSTox_CID_26051, DSSTox_RID_81307, DSSTox_GSID_46051, CAS-608-66-2, WURCS=1.0/1,0/[h1221h], Melampyrite, Melampyrum, NCGC00159410-03, NCGC00159410-04, Ambap5938, Epitope ID:114704, AC1L1YA0, UNII-113ZQ1Y7DD, Ambap608-66-2, SCHEMBL25162, D0256_SIGMA, 113ZQ1Y7DD, AC1Q59P0, CHEMBL1773904, HMDB00107, MolPort-003-933-102, NSC 1944, EINECS 210-165-2, Tox21_111643, Tox21_111644, ZINC18006959, AKOS008145350, Tox21_111643_1, Tox21_111644_1, MCULE-5520163874, NCGC00164353-05, NCGC00166072-02, AJ-70222, AK113597, CA001769, AI3-19423, G0005, ST24020272, A-8035, C01697, 118FFB2B-9CDF-4CF4-9706-6865B46BA004, 18089-21-9, 362631-40-1, 40742-76-5

Removed Synonyms

sorbitol, Hexitol, CID11850

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