Isovanillic Acid → Ethyl 3-hydroxy-4-methoxybenzoate

HRID 337247Notes

Reaction equation

HRID 337247 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].O.[C:14]1(C)C=CC(S(O)(=O)=O)=C[CH:15]=1>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH2:14][CH3:15])=[O:6]

Participants

4

Reactant 2

HCID 12575Isovanillic AcidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 15480330Ethyl 3-hydroxy-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-Hydroxy-4-methoxybenzoic acid (25 g, 148.67 mmol) and p-Toluenesulfonic acid monohydrate (3.17 g, 16.66 mmol) in abs ethanol (300 ml) was refluxed for 6 hours or until all the starting material is consumed. The reaction mixture was concentrated, diluted with EtOAc (60 ml) and washed with water (20 ml). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound.

Workup

  1. customis consumed
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with EtOAc (60 ml)
  4. washwashed with water (20 ml)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

Sources & evidence

ORD record
ord-ccfa45685b7348dcad4cb351c80d8504
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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