Process for the preparation of hydroxy substituted gamma butyrolactones
AssigneeBoard of Trustees of Michigan State University
InventorRawle I. Hollingworth
Life of this patent
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Abstract
Preparation of 4-hydroxy substituted butyrolactones is described. A process for the preparation of 3-hydroxybutyrolactone, 1.2.4-trihydroxybutane and 3,4-dihydroxy acid methyl ester from malic acid is particularly described. The preparation of 4-hydroxymethyl-4-hydroxybutyric acid -1-methyl ester and 4-hydroxymethyl butyrolactone is particularly described. The compounds are intermediates to various pharmaceutical and agricultural products.
Claims34
A process for producing a hydroxy substituted compound which comprises:
- reacting in a reaction mixture a 2-hydroxy substituted alkane diacid lower alkyl diester wherein the diacid contains 4 to 8 carbon atoms and alkyl contains 1 to 4 carbon atoms, with an alkali metal borohydride in a non-reactive solvent to produce the hydroxy substituted compound.
A process for the preparation of a hydroxy substituted gamma butyrolactone which comprises:
- reading in a reaction mixture a 2-hydroxy substituted alkane diacid lower alkyl diester, wherein the diacid contains 4 in 5 carbon atoms and alkyl contains 1 to 4 carbon atoms, with an alkali metal borohydride in a non-reactive solvent at a temperature between about −10° and 60° C. to produce the hydroxy substituted gamma butyrolactone and an alcohol as a by-product.
A process for the preparation of a compound selected from the group consisting of 1,2,4-trihydroxybutane and 3,4-dihydroxybutyric acid -1-methyl ester and mixtures thereof which comprises:
- (a) reacting in a reaction mixture malic acid with a molar excess of anhydrous methanol in the presence of a catalytic mount of hydrogen ion end at a temperature between about 40° and reflux to produce hydroxybutane dioic acid di methyl ester;
- and
- (b) reducing the hydroxybutane dioic acid dimethyl ester with an alkali metal borohydride to produce the compound.
A process for the preparation of 3,4-dihydroxybutyric acid-1-methyl ester which comprises:
- (a) reacting in a reaction mixture malic acid with a molar excess of anhydrous methanol in the presence of a catalytic amount of hydrogen ion and at a temperature between about 40° and reflux to produce hydroxybutane dioic acid dimethyl ester;
- and
- (b) reducing the hydroxybutane dioic acid dimethyl ester with an alkali metal borohydride to produce the 3,4-dihydroxybutyric acid-1-methyl ester.
Dependencies are inferred from the claim text.