Reaction equation
[CH3:1][C@@H:2]([OH:7])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+]>>[OH:7][C@H:2]([CH3:1])[CH2:3][C:4]([OH:6])=[O:5].[OH:7][C@H:2]([CH3:1])[CH2:3][C:4]([OH:6])=[O:5]Participants
3
Procedure
(R)-3-hydroxybutyric acid (Fluka-5.0 g: 0.048 mole), p-toluene sulphonic acid (0.025 g) and benzene (100 ml) were stirred under reflux withn a Dean-Stark trap arrangement for 24 hours. The reaction mixture was cooled and the benzene evaporated in vacuo (0.5 mm Hg). 4.4 g of colourless oil was obtained of which a 20 mg sample was converted to the methyl ester for analysis of number of monomer repeats using NMR. These studies show that the product is a mixture of oligomers of D-β-hydroxybutyrate of average number of repeats 3.75, being mainly a mixture of trimers, tetramers and pentamers with the single most abundant material being the tetramer. The product mixture was soluble in 1 equivalent of sodium hydroxide.
Workup
- additiona mixture of trimers, tetramers and pentamers with the single most abundant material
Sources & evidence
- ORD record
- ord-debe321d3d8d417bacf31e8d769058c5
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351736B2
Linked notes
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