Methanol → Methyl 2-hydroxy-4-(methylthio)benzoate

HRID 1434824Notes

Reaction equation

HRID 1434824 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:17]O>>[OH:1][C:2]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 134507492-Hydroxy-4-(methylsulfanyl)benzoic acid

Product 1

HCID 13450750Methyl 2-hydroxy-4-(methylthio)benzoateYield 63%

Conditions

Temperature
65 °C

Procedure

The 2-hydroxy-4-(methylthio)benzoic acid (836 mg, 4.54 mmol) was dissolved in MeOH (45 mL). Thionyl chloride (0.35 mL, 4.80 mmol) was added and the solution was heated to 65° C. and left overnight. TLC indicated that there was still starting material present; so more thionyl chloride (1.0 mL, 13.7 mmol) was added. After about 1.5 hour, TLC indicated formation of baseline material; so the reaction was concentrated in vacuo. The crude residue was purified using flash column chromatography (100% CH2Cl2) to give the desired compound as an off-white solid (567 mg, 2.86 mmol, 63%).

Workup

  1. waitAfter about 1.5 hour
  2. concentrationso the reaction was concentrated in vacuo
  3. customThe crude residue was purified

Sources & evidence

ORD record
ord-0764e117e9424a0da3c3bf0472a0d855
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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