Ethyl Acetate → HCID 66756203, compound

HRID 1642011Notes

Reaction equation

HRID 1642011 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:13]=[CH:14][C:15]=1[N+]([O-])=O)[C:9]([O:11][CH3:12])=[O:10].[CH3:20][S-:21].[Na+].C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:13]=[CH:14][C:15]=1[S:21][CH3:20])[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolateHCID 66755899HCID 66755899, compound

Product 1

HCID 66756203HCID 66756203, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-(2-methoxyethoxy)-2-methyl-4-nitrobenzoate (31 g) was dissolved in anhydrous DMF (300 mL), and sodium thiomethoxide (purity: 95%, 8.92 g) was added at room temperature, followed by stirring for 45 minutes. To the reaction mixture, ethyl acetate (400 mL) was added and washed once with 1 N hydrochloric acid (150 mL) and washed twice with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylthio)benzoate (30 g) as a solid.

Workup

  1. washwashed once with 1 N hydrochloric acid (150 mL)
  2. washwashed twice with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-03428c4cb2874d2698f3700c1b443c03
Source dataset
uspto-grants-2012_02
Patent number
US08119569B2

Reaction notes

Loading…