4-Toluenesulfonyl chloride → 4-Phenoxy-2-butyl tosylate

HRID 1632300Notes

Reaction equation

HRID 1632300 reaction equation
[O:1]([CH2:8][CH2:9][CH:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[OH-].[Na+]>>[S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)([O:12][CH:10]([CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:11])(=[O:21])=[O:20]

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 113787034-Phenoxy-2-butanol

Product 1

HCID 133267624-Phenoxy-2-butyl tosylateYield 98%

Procedure

10 g of the 4-phenoxy-2-butanol was reacted with 13.9 g of p-toluenesulfonyl chloride in 21.2 ml of 5N-sodium hydroxide in accordance with the method described in Norris, J. Am. Chem. Soc. 38, 642 (1907) to obtain 18.9 g of 4-phenoxy-2-butyl tosylate having a boiling point of 170° C. to 171° C. at 2 mmHg in a yield of 89%.

Sources & evidence

ORD record
ord-e0431f6eec614272b3da2b0757a54434
Source dataset
uspto-grants-1984_10
Patent number
US04474964

Reaction notes

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