Methanol → Methyl 2-methoxy-5-methylthiobenzoate

HRID 323390Notes

Reaction equation

HRID 323390 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 HexaneSolvent2×

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-0b63e3f4f22544b58af8d7db58045c38
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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