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ChemicalBook CAS DataBase List 1,3-Dihydroxyacetone

1,3-Dihydroxyacetone synthesis

15synthesis methods
1,3 dihydroxyacetone is useful in various products, including as a sunless tanning agent.A synthesis comprising reacting glycerol with acetaldehyde or 1,1-diethoxyethane to produce 1,3-dihydroxyacetone (DHA), without using fermentation or direct oxidation of the glycerol is provided. 
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Yield:96-26-4 95%

Reaction Conditions:

with 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in water;acetonitrile at 60; under 760.051 Torr; for 12 h;

Steps:

1
Glycerol (1.0 mmol) and TEMPO (2.0 mmol) were placed in a flask under an air atmosphere (1 atm) and dissolved by adding a mixed solvent of 1 mL of water and 3 mL of acetonitrile. Here, 50 mg (containing Cu 2 +: 4.5 mg) of "Cu (II) -AlO (OH)" obtained in Preparation Example 1 was added and the reaction was carried out at 60 ° C. for 12 hours. The reaction progresses to TLC (I2 coloration) I monitored. After completion of the reaction, the reaction solution was centrifuged to remove "Cu (II) -AlO (OH)" and the supernatant was passed through a silica gel column (acetone eluent) to remove TEMPO, And concentrated to isolate a pale yellow oily reaction product. HPLC of the reaction product, 1 H-NMR, and As a result of 13 C-NMR analysis, It was confirmed to be dihydroxyacetone, The raw material conversion was 100%, and the yield of dihydroxyacetone was 95%.

References:

DAICEL CORPORATION;OSAKA UNIVERSITY;KANEDA, KIYOTOMI;MATSUDA, HIROKAZU JP6099133, 2017, B2 Location in patent:Paragraph 0051

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