ChemicalBook CAS DataBase List (1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE

(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE synthesis

10synthesis methods

Product Name:(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE
CAS Number:1517-82-4
Molecular formula:C17H26O2S
Molecular Weight:294.45

536-57-2 Synthesis

536-57-2
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$34.00/1g

2216-51-5
670 suppliers
$5.00/100mg

(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE

1517-82-4
121 suppliers
$21.00/1g

Yield: 99%

Reaction Conditions:

with dmap;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane at 25; for 16 h;Inert atmosphere;Temperature;Reagent/catalyst;

Steps:

4-Bromobenzyl p-Toluenesulfinate (1c), Typical Procedure
General procedure: To a 250 mL flame-dried N₂ purged round-bottomed flask was added p-toluenesulfinic acid (0.525 g, 3.36 mmol), 4-bromobenzyl alcohol (0.598 g, 3.20 mmol), and DMAP (0.078 g, 0.64 mmol) sequentially and dissolved in anhyd CH₂Cl₂ (14 mL). To the solution was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.644 g, 3.36 mmol) in one portion and stirred for 16 h at r.t. The reaction mixture was diluted with CH₂Cl₂ (30 mL) and washed with aq 1 M HCl (30 mL) and brine (30 mL). The organic layer was dried (MgSO4), filtered, and solvents removed under reduced pressure. The crude product was purified by flash column chromatography .

References:

Gafur, Sayed Habibul;Waggoner, Stephanie L.;Jacobsen, Eric;Hamaker, Christopher G.;Hitchcock, Shawn R. [Synthesis,2018,vol. 50,# 24,art. no. SS-2018-M0396-OP,p. 4855 - 4866]