Methanol → Methyl 4-hydroxy-1-naphthoate

HRID 1166721Notes

Reaction equation

HRID 1166721 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:19]O>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:19])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 3442911-Hydroxy-4-naphthoic acid

Product 1

HCID 22171384Methyl 4-hydroxy-1-naphthoate

Procedure

To a solution 4-hydroxynaphthoic acid in anhydrous methanol at 0° C. was added thionyl chloride (1.5 eq). After stirring the solution at room temperature for 16 hours, the solvent was evaporated. The residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate, water, brine, and dried over MgSO4 to give methyl 4-hydroxynaphthoate.

Workup

  1. customthe solvent was evaporated
  2. washwashed with saturated aqueous sodium bicarbonate, water, brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d1aa3811e28248218b85d5b7c8088c27
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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