Methanol → Methyl 6-hydroxy-2-naphthoate

HRID 1072106Notes

Reaction equation

HRID 1072106 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.S(=O)(=O)(O)O.[CH3:20]O>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:20])=[O:13])[CH:6]=[CH:5]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 390995Methyl 6-hydroxy-2-naphthoateYield 84%

Procedure

15.7 g (83 mmol) of 6-hydroxy-2-naphthoic acid in 160 ml of methanol are introduced into a round-bottomed flask. 8 ml of concentrated sulphuric acid are added and the mixture is heated under reflux for 8 hours. At room temperature, a precipitate forms. It is filtered off, rinsed with ether and dried. 14.1 g (84%) of the expected product are obtained in the form of a beige powder.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 8 hours
  3. customAt room temperature
  4. filtrationIt is filtered off
  5. washrinsed with ether
  6. customdried

Sources & evidence

ORD record
ord-551019b02728401c829e6373bf00a827
Source dataset
uspto-grants-2005_06
Patent number
US06908939B2

Reaction notes

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