Methanol → Methyl 6-hydroxy-1-naphthoate

HRID 1925360Notes

Reaction equation

HRID 1925360 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 ChlorideHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 11367671Methyl 6-hydroxy-1-naphthoate

Conditions

Temperature
22.5 °C

Procedure

To a cooled solution of 6-hydroxy-1-napthoic acid (TCI America) (50 g, 0.27 mmol) in methanol (500 mL), thionyl chloride (29 mL, 0.40 mmol) was added slowly. The temperature was maintained at 15 to 30° C. The reaction mixture was allowed to warm to RT and stirred O/N. The solvent was concentrated in-vacuo and the residue azeotroped with benzene. The title compound was obtained as a pink solid.

Workup

  1. temperatureto warm to RT
  2. concentrationThe solvent was concentrated in-vacuo
  3. customthe residue azeotroped with benzene

Sources & evidence

ORD record
ord-719543c2b0f543b89722249026a4515f
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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