Hydrochloric Acid → HCID 18470626, compound

HRID 2228498Notes

Reaction equation

HRID 2228498 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[C:6]([O:20]S(C)(=O)=O)=[C:7]([C:12]([N+:17]([O-:19])=[O:18])=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([O:10][CH3:11])=[O:9].Cl>O1CCOCC1>[CH3:3][O:4][C:5]1[C:6]([OH:20])=[C:7]([C:12]([N+:17]([O-:19])=[O:18])=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18470639HCID 18470639, compound

Product 1

HCID 18470626HCID 18470626, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4N aqueous sodium hydroxide solution (17 ml) was added to an ice cooled suspension of methyl 3,4-dimethoxy-2-methanesulfonyloxy-6-nitrobenzoate (1.74 g, 0.0052 mol) in dioxane (9 ml) and the resulting orange solution stirred for 1 hour. The reaction mixture was acidified with 2N aqueous hydrochloric acid and extracted with dichloromethane (2×50 ml). The combined organic extracts were dried (MgSO4), filtered and evaporated under reduced pressure to give the subtitle compound as a white solid (1.23 g, 92%). MS m/z 275 (MNH4)+. 1H-NMR (CDCl3): Γ=3.92 (9H, m), 6.86 (1H, s), 9.66 (1H, s).

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane (2×50 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c64c0070c39041b7a1cceac79ca39146
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

Loading…