Isovanillic Acid → Ethyl 3-hydroxy-4-methoxybenzoate

HRID 1958842Notes

Reaction equation

HRID 1958842 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-970c97a424ab4b639647ee3caa7ec95c
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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