Methanol → Methyl 3-hydroxy-4-methoxybenzoate

HRID 1831772Notes

Reaction equation

HRID 1831772 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:9]([OH:11])=[O:10].[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:6]([OH:5])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 12575Isovanillic AcidHCID 24386Thionyl Chloride

Product 1

HCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Conditions

Temperature
50 °C

Procedure

10 ml of thionyl chloride was added to 250 ml of MeOH at 0° C. The solution was stirred for 10 min. and 25 g of 3-hydroxy-4-methoxybenzoic acid was added. The reaction was stirred for 16 h at RT then heated to 50° C. for 3 h. The solvents were removed under reduced pressure. The residue was directly used in the next reaction.

Workup

  1. stirringThe reaction was stirred for 16 h at RT
  2. customThe solvents were removed under reduced pressure
  3. customThe residue was directly used in the next reaction

Sources & evidence

ORD record
ord-387a9733dabc45469ee4f9dab13a7cb2
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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