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

HRID 2405630Notes

Reaction equation

HRID 2405630 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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1128Tetramethylene sulfoxideHCID 70051-Naphthol

Product 1

HCID 714422161-(4-Hydroxynaphthalen-1-yl)thiolan-1-ium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

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

Sources & evidence

ORD record
ord-d75f7b9299924b65a9696eb925145fcb
Source dataset
uspto-grants-2014_08
Patent number
US08808964B2

Reaction notes

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