Methanol → Methyl 4-hydroxy-2-methoxybenzoate

HRID 2204207Notes

Reaction equation

HRID 2204207 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([O:15][CH3:16])[CH:7]=1.[CH3:17]O>>[OH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:17])=[O:11])=[C:8]([O:15][CH3:16])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 126955754-Hydroxy-2-methoxybenzoic acid

Product 1

HCID 12532676Methyl 4-hydroxy-2-methoxybenzoateYield 99%

Conditions

Temperature
50 °C

Procedure

Thionyl chloride (953 μL, 13.1 mmol) was added dropwise to a solution of 4-hydroxy-2-methoxy-benzoic acid (733 mg, 4.36 mmol) in methanol (30 mL) at 0° C. The mixture was stirred at 50° C. overnight. The reaction mixture was concentrated and the residue was dissolved in water (40 mL). The solution was neutralized with saturated sodium bicarbonate solution and the product was extracted into ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated to dryness to give methyl 4-hydroxy-2-methoxy-benzoate (99%). ESI-MS m/z calc 182.1, found 183.1 (M+1)+. Retention time: 0.73 minutes (3 min run).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water (40 mL)
  3. extractionthe product was extracted into ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-7108a98afd864f8a8da4eb111cb27052
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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