Methanol → Methyl 6-hydroxy-1-naphthoate

HRID 908322Notes

Reaction equation

HRID 908322 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2.S(Cl)(Cl)=O.[CH3:19]O>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:19])=[O:13])=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 11367671Methyl 6-hydroxy-1-naphthoate

Procedure

To a solution of 6-Hydroxy-1-naphthoic acid (6.9 g. 37 mmol) in 200 mL of MeOH at 0° C. was added drop wise over 5 minutes thionyl chloride (3.26 mL). The resulting mixture was stirred overnight at room temperature and another 2.5 mL of Thionyl chloride was added and mixture was stirred at room temperature. Solvent was evaporated and residue was dried under vacuo to give 7.49 g the title compound as a brown solid.

Workup

  1. stirringmixture was stirred at room temperature
  2. customSolvent was evaporated
  3. customresidue was dried under vacuo

Sources & evidence

ORD record
ord-de3e97f7a1e24f5d99ea50baf5774509
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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