Hydrochloric Acid → 1-(4-Hydroxynaphthalen-1-yl)thiolan-1-ium chloride

HRID 41842

Reaction equation

[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]1[S:16](=O)[CH2:15][CH2:14][CH2:13]1.[ClH:18]>CO>[Cl-:18].[OH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([S+:16]2[CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -16 °C

Procedure

In 50 g of methanol were dissolved 10 g (0.069 mol) of 1-naphthol and 7.2 g (0.069 mol) of tetramethylene sulfoxide. The solution was cooled to −16° C. An excess of hydrogen chloride gas was fed to the solution at a temperature below 20° C. Nitrogen gas was bubbled to expel the excess of hydrogen chloride. The reaction solution was concentrated and combined with water and diisopropyl ether, from which a water layer was separated. It was an aqueous solution of 4-hydroxynaphthyl-1-tetrahydrothiophenium chloride. This aqueous solution was used in the subsequent step without further isolation.

Workup

customwas fed to the solution at a temperature below 20° C
customNitrogen gas was bubbled
concentrationThe reaction solution was concentrated
customwas separated

Sources & evidence

ORD record: ord-1158d82d9aa24d7db4dbdc5a06a5f6fd
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08535869B2

Linked notes

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