4-Toluenesulfonyl chloride → (2R)-2-methoxypropyl 4-methylbenzene-1-sulfonate

HRID 974875Notes

Reaction equation

HRID 974875 reaction equation
[CH3:1][O:2][C@H:3]([CH3:6])[CH2:4][OH:5].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>N1C=CC=CC=1>[CH3:1][O:2][C@H:3]([CH3:6])[CH2:4][O:5][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 27335882-Methoxy-1-propanol, (2R)-

Product 1

HCID 13896527(2R)-2-methoxypropyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

By reacting (-)-(R)-2-methoxypropanol with p-toluenesulphonic acid chloride in pyridine analogously to R. S. Tipson [J. Org. Chem. 9 (1944) 235] the (+)-(R)-2-methoxypropyl-p-toluenesulphonate is obtained in the form of a yellowish oil with a specific rotation of [α]D25 =+3.7° (c=100) and analogously, from (+)-(S)-2-methoxy-propanol, the corresponding (-)-(S)-2-methoxypropyl-p-toluenesulphonate is obtained with a rotation of [α]D25 =-3.7° (c=100).

Sources & evidence

ORD record
ord-86d6c63011fe4871ba870507bea45784
Source dataset
uspto-grants-1997_03
Patent number
US05607941

Reaction notes

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