Sodium Chloride → Methyl 3-isopropoxy-4-(methylthio)benzoate

HRID 356970Notes

Reaction equation

HRID 356970 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[N+]([O-])=O)[C:8]([O:10][CH3:11])=[O:9])([CH3:3])[CH3:2].[CH3:18][S-:19].[Na+].[Cl-].[Na+]>CN1CCN(C)C1=O.O>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[S:19][CH3:18])[C:8]([O:10][CH3:11])=[O:9])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 4378561Sodium methanethiolateHCID 21187964Methyl 3-isopropoxy-4-nitrobenzoate

Product 1

HCID 21187888Methyl 3-isopropoxy-4-(methylthio)benzoateYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

A solution of methyl 3-isopropoxy-4-nitrobenzoate (5.7 g) in N,N'-dimethylimidazolidinone (35 mL) is treated with sodium thiomethoxide (2 g), and the mixture is stirred at room temperature for 4 hours. The mixture is then diluted with water (250 mL) containing sodium chloride (47 g), and is extracted with ethyl acetate (2×100 mL). The combined organic extracts are washed with brine (100 mL), dried over magnesium sulfate and evaporated in vacuo, to give a brown oil. The oil is subjected to flash chromatography, eluting with a 1.9 v/v mixture of diethyl ether and pentane, to give methyl 3-isopropoxy-4-(methylthio)benzoate (4.0 g), in the form of a cream solid, m.p. 41°-43° C.

Workup

  1. extractionis extracted with ethyl acetate (2×100 mL)
  2. washThe combined organic extracts are washed with brine (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give a brown oil
  6. washeluting with a 1.9 v/v mixture of diethyl ether and pentane

Sources & evidence

ORD record
ord-7ada88d3caa14c2c95ac0aacefe07e4f
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

Loading…