Dihydroxyacetone → 1,3-Dibutyrin

HRID 1906914Notes

Reaction equation

HRID 1906914 reaction equation
[OH:1][CH2:2][C:3]([CH2:5][OH:6])=[O:4].[C:7](Cl)(=[O:11])[CH2:8][CH2:9][CH3:10]>N1C=CC=CC=1>[C:7]([O:1][CH2:2][CH:3]([OH:4])[CH2:5][O:6][C:7](=[O:11])[CH2:8][CH2:9][CH3:10])(=[O:11])[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 670DihydroxyacetoneHCID 8855Butyryl chloride

Product 1

HCID 1229201,3-Dibutyrin

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

By following the procedure of Example 1(a) and 1(b) using 13.05 g. of 1,3-dihydroxyacetone, 23.7 g. of pyridine and 31.1 g. of butyryl chloride, 17.9 g. of 1,3-dibutanoyloxy-2-propanol is obtained. The reaction of 12.2 g. of this material and 9.4 g. of valproyl chloride and 4.98 g. of pyridine as described in Example 1(c) yields an oil which is purified by chromatography as described in Example 3. The pure 1,3-dibutanoyl-2-valproyl-glyceride is eluted from the column with petroleum ether/ether (95:5); it is obtained in a yield of 9.1 g.; Rf 0.61 (petroleum ether/ether 3:1); mass spectrum m/e 316 (M+ -42).

Sources & evidence

ORD record
ord-0d533ae828c945839b89498cd6af0d14
Source dataset
uspto-grants-1987_03
Patent number
US04654370

Reaction notes

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