Hydrochloric Acid → 2-(2-Methanesulfonyloxyethyl)-5,6,7-trimethoxynaphthalene

HRID 987420Notes

Reaction equation

HRID 987420 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:18][CH3:19])=[C:9]([O:16][CH3:17])[C:10]=2[O:14][CH3:15])[CH:5]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].Cl>N1C=CC=CC=1>[CH3:20][S:21]([O:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:18][CH3:19])=[C:9]([O:16][CH3:17])[C:10]=2[O:14][CH3:15])[CH:5]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 218915912-(2-Hydroxyethyl)-5,6,7-trimethoxynaphthalene

Product 1

HCID 218915682-(2-Methanesulfonyloxyethyl)-5,6,7-trimethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(2-Hydroxyethyl)-5,6,7-trimethoxynaphthalene (1.26 g) was dissolved in pyridine (5 mL), methanesulfonyl chloride (715 mg) was added at 0° C. to the solution, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The resultant extract was washed with water and saturated brine. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:5) to obtain the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe resultant extract
  3. washwas washed with water and saturated brine
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-fdf21c993a7944ab8c2f4e1f9167b102
Source dataset
uspto-grants-2003_10
Patent number
US06632810B2

Reaction notes

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