ChemicalBook CAS DataBase List (S)-(+)-3-Chloro-1,2-propanediol

(S)-(+)-3-Chloro-1,2-propanediol synthesis

10synthesis methods

Product Name:(S)-(+)-3-Chloro-1,2-propanediol
CAS Number:60827-45-4
Molecular formula:C3H7ClO2
Molecular Weight:110.54

67843-74-7
474 suppliers
$10.00/1g

60827-45-4
258 suppliers
$14.00/5g

Yield:60827-45-4 95.4 %Chromat.

Reaction Conditions:

Stage #1: with N,N'-bis(3,5-di-tert-butylsalicylidene)ethylenediaminocobalt(II);camphor-10-sulfonic acid;oxygen in tetrahydrofuran for 1 h;
Stage #2:(S)-epichlorohydrin with water in tetrahydrofuran at 20; for 20 h;

Steps:

1 Example 1; Preparation of (S)-3-chloro-1,2-propanediol
Example 1 Preparation of (S)-3-chloro-1,2-propanediol To a mixture of N',N'-bis(3,5-di-tertbutylsalicylidene) ethylenediaminatocobalt(II) (119 mg, 0.216 mmol) and tetrahydrofuran (THF) (2.0 ml) was added (+) camphorsulfonic acid (60.3 mg, 0.260 mmol) and the reaction system was stirred for 1 hour while being filled with air.Thereto, namely to cobalt (III) complex in THF solution was added (S)-epichlorohydrin (1.00 g, 10.8 mmol, optical purity 99% e.e.) and water (234 μl, 13.0 mmol) in order, and the mixture was stirred for 20 hours at room temperature.After the reaction, quantitative analysis and optical purity measurement were conducted by gas chromatography on the reaction solution.As a result the subject compound, (S)-3-chloro-1,2-propanediol. (1.14 g, 95.4%) was produced with optical purity at 99% e.e.

References:

Yaegashi, Keisuke;Furukawa, Yoshiro US2004/24254, 2004, A1 Location in patent:Page 4

106-89-8 Synthesis