Hydrochloric Acid → Methyl 4-methoxy-3-propyl-5-sulfanylbenzoate

HRID 638945Notes

Reaction equation

HRID 638945 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[C:7]([O:13][CH3:14])=[C:6]([S:15]C(OCC)=S)[CH:5]=1.CO[Na].Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[C:7]([O:13][CH3:14])=[C:6]([SH:15])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86618871HCID 86618871, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 68685440Methyl 4-methoxy-3-propyl-5-sulfanylbenzoateYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-ethoxythiocarbonylthio-4-methoxy-5-propylbenzoic acid methyl ester (720 mg, 2.20 mmol) in THF (13 mL) at room temperature was added MeONa (0.5 M in MeOH, 13 mL, 6.5 mmol, 3 eq.). The reaction mixture was refluxed for 75 min, then cooled to room temperature and added to 1 N HCl aqueous solution (100 mL). The resulting mixture was extracted with EtOAc/hexanes (1:1, 100 mL). The organic layer was washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo to give 3-mercapto-4-methoxy-5-propylbenzoic acid methyl ester (0.55 g). The product was used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 75 min
  2. extractionThe resulting mixture was extracted with EtOAc/hexanes (1:1, 100 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3dc28e7c8a41444f93d3df05e7a130f3
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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