Methanol → Methyl 6-hydroxy-2-naphthoate

HRID 720803Notes

Reaction equation

HRID 720803 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.OS(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 95%

Procedure

To a 1-L round bottomed flash equipped with a nitrogen inlet and magnetic stir bar was added 50 g (0.27 mol) of 6-hydroxy-2-naphthoic acid and 400 mL of methanol. The suspension was treated slowly with 1 mL of con. H2SO4 and stirred at room temperature overnight. The resulting solution was evaporated, taken up in 500 mL of ethyl acetate and washed sequentially with 3×300 mL of saturated NaHCO3, 2×300 mL of water and brine. The pale yellow solution was dried over MgSO4, reduced in volume to about 100 mL and slowly treated with hexane. The resulting crystalline precipitate was collected and dried under a stream of nitrogen to yield 52 g (95%) of the title compound as fine, white plates, mp 196° C.

Workup

  1. customTo a 1-L round bottomed flash equipped with a nitrogen inlet and magnetic stir bar
  2. additionThe suspension was treated slowly with 1 mL of con
  3. customThe resulting solution was evaporated
  4. washwashed sequentially with 3×300 mL of saturated NaHCO3, 2×300 mL of water and brine
  5. dry with materialThe pale yellow solution was dried over MgSO4
  6. additionslowly treated with hexane
  7. customThe resulting crystalline precipitate was collected
  8. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-e90cce91330345acb6ad8a0e9b0d244a
Source dataset
uspto-grants-2006_11
Patent number
US07135595B2

Reaction notes

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