4-Toluenesulfonyl chloride → (S)-(+)-2-Hydroxypropyl P-toluenesulfonate

HRID 350627Notes

Reaction equation

HRID 350627 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:12])[C@@H:9]([OH:11])[CH3:10].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C(Cl)Cl>[OH:11][C@@H:9]([CH3:10])[CH2:8][O:12][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 439846(S)-propane-1,2-diol

Product 1

HCID 10955373(S)-(+)-2-Hydroxypropyl P-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Triethylamine was added to methylene chloride solution of (2S)-propane-1,2-diol, and then methylene chloride solution of p-toluenesulfonyl chloride was added thereto at −20° C. and stirred at room temperature for 18 hours to obtain (2S)-2-hydroxypropyl-4-methylbenzene sulfonate.

Sources & evidence

ORD record
ord-4c016f27fc134487ae4e8daebab5053f
Source dataset
uspto-grants-2007_02
Patent number
US07183271B2

Reaction notes

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