1-Methoxynaphthalene → 4-Methoxynaphthalene-1-sulfonyl chloride

HRID 1174516Notes

Reaction equation

HRID 1174516 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[Cl:13][S:14](O)(=[O:16])=[O:15].P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 166681-MethoxynaphthaleneHCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 167755014-Methoxynaphthalene-1-sulfonyl chlorideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 1-methoxy naphthalene (5 cm3, 34.5 mmol) in dichloromethane (20 cm3) was added, over a 10 minute period, chlorosulfonic acid (4.6 cm3, 69.0 mmol). Following this addition, phosphorus pentachloride (7.2 g, 34.5 mmol) was added and the reaction was maintained at 0° C. for a further 45 min. The reaction was then quenched by pouring onto ice/water (50 cm3), and allowed to warm to room temperature. Further dichloromethane (40 cm3) was added and the solution was transferred to a separating funnel, where the organic layer was collected and washed with saturated aqueous sodium chloride solution (70 cm3) and dried over sodium sulfate. The solvent was then evaporated under reduced pressure to afford title compound (8.23 g, 32.1 mmol; 93%).

Workup

  1. additionwas added, over a 10 minute period
  2. additionwas added
  3. customThe reaction was then quenched
  4. additionby pouring onto ice/water (50 cm3)
  5. temperatureto warm to room temperature
  6. additionFurther dichloromethane (40 cm3) was added
  7. customthe solution was transferred to a separating funnel
  8. customwhere the organic layer was collected
  9. washwashed with saturated aqueous sodium chloride solution (70 cm3)
  10. dry with materialdried over sodium sulfate
  11. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-ff5fed65b705401ea351cd4fc666e559
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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