Hydrochloric Acid → 4-Methoxyphenyl 4-methoxy-1-naphthyl sulfone

HRID 1087958Notes

Reaction equation

HRID 1087958 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.ClC1C=CC=CC=1Cl.Cl>[N+](C)([O-])=O>[CH3:13][O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([S:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)(=[O:11])=[O:10])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72391,2-DichlorobenzeneHCID 74014-Methoxybenzenesulfonyl chlorideHCID 166681-Methoxynaphthalene

Product 1

HCID 162262124-Methoxyphenyl 4-methoxy-1-naphthyl sulfoneYield 88%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

p-Methoxybenzenesulfonyl chloride, 2.0 mol, anhydrous stannic chloride, 2.25 mol, 1-methoxynaphthalene, 2.25 mol, and 3 l of o-dichlorobenzene were mixed at room temperature under nitrogen. The mixture was stirred at room temperature overnight (ca 7 hours needed) and decomposed with 3N hydrochloric acid. The organic layer was diluted with 1250 ml of nitromethane and washed with 2 portions of 1N hydrochloric acid followed by pure water. The organic layer was treated with magnesium sulfate, filtered, evaporated, extracted with hot toluene and dried at 120° c. for two hours to give 577 g, 88% yield, m.p. 160°-162° C.

Workup

  1. washwashed with 2 portions of 1N hydrochloric acid
  2. additionThe organic layer was treated with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. extractionextracted with hot toluene
  6. customdried at 120° c
  7. customfor two hours to give 577 g, 88% yield, m.p. 160°-162° C.

Sources & evidence

ORD record
ord-274bb973e14d4fc6a5a8d4fd089cbb97
Source dataset
uspto-grants-1990_10
Patent number
US04960912

Reaction notes

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