Hydrochloric Acid → 2-(Hexyloxy)ethyl 4-methylbenzenesulfonate

HRID 2120504Notes

Reaction equation

[CH2:1]([O:7][CH2:8][CH2:9][OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].N1C=CC=CC=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl>>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:10][CH2:9][CH2:8][O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 1049Pyridine

HCID 73974-Toluenesulfonyl chloride

HCID 81702-Hexyloxyethanol

Product 1

HCID 132797162-(Hexyloxy)ethyl 4-methylbenzenesulfonateYield 95.6%

Procedure

Into a reaction vessel, 3.29 g (22.5 mmol) of 2-hexyloxyethanol and 5.33 g (67.5 mmol) of pyridine were charged, and 4.72 g (24.7 mmol) of p-toluenesulfonic acid chloride was added thereto in an ice bath, which were then stirred for 1 hour and thereafter further stirred at room temperature for 3 hours. After the reaction was completed, 3N HCl was added to make the reaction mixture acidic, followed by extraction with toluene twice. The extract obtained was washed with water, and thereafter sodium sulfuric anhydride was added to effect drying. After the solvent was evaporated off, the resultant mixture was purified by silica gel chromatography (eluting solvent: toluene/ethyl acetate=10/1) to obtain 6.45 g (21.5 mmol) of 2-hexyloxyethyl p-toluenesulfonate. Yield: 95%.

Workup

stirringfurther stirred at room temperature for 3 hours
extractionfollowed by extraction with toluene twice
customThe extract obtained
washwas washed with water
additionsodium sulfuric anhydride was added to effect
customdrying
customAfter the solvent was evaporated off
customthe resultant mixture was purified by silica gel chromatography (eluting solvent: toluene/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-d2e2fabafb404c338a52e54b11c462f1
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06692658B2

Reaction notes

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