Methanol → Methyl 2-methoxy-5-methylthiobenzoate

HRID 637124Notes

Reaction equation

HRID 637124 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:4]=1[C:5]([OH:7])=[S:6].[CH3:13]O.S(Cl)(Cl)=O>CCCCCC.ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:4]=1[C:5]([O:7][CH3:13])=[S:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178489964HCID 178489964, compound

Product 1

HCID 53727199Methyl 2-methoxy-5-methylthiobenzoate

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

Combine 2-methoxy-5-methylthiobenzoic acid (6.82 g, 34.4 mmol) and methanol (65 mL). Cool in an ice bath. Add slowly dropwise thionyl chloride (2.8 mL, 38 mmol). Warm to ambient temperature. After 18 hours, evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 25% hexane/dichloromethane to give methyl 2-methoxy-5-methylthiobenzoate: Rf=0.06 (silica gel, 65% hexane/dichloromethane).

Workup

  1. temperatureCool in an ice bath
  2. customevaporate in vacuo
  3. customto give a residue

Sources & evidence

ORD record
ord-6b0b09a066dd4ea0b855f9b5cd278faf
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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