p-Toluenesulfonic acid → Methyl 3,5-dihydroxy-2-naphthoate

HRID 1369281Notes

Reaction equation

HRID 1369281 reaction equation
[OH:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2.[CH3:16]C1C=CC(S(O)(=O)=O)=CC=1.C(OC)(OC)OC.C([O-])(O)=O.[Na+]>CO.OS(O)(=O)=O>[OH:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 666373,5-Dihydroxy-2-naphthoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11746080Methyl 3,5-dihydroxy-2-naphthoateYield 4,404.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3,5-dihydroxy-2-naphthoic acid (5.05 g) in MeOH (100 mL) was added TsOH (93 mg). Tho reaction mixture was stirred at reflux for 18 hours and then CH(OMe)3 (1 mL) was added. The reaction mixture was stirred at reflux for an additional 5 hours, at which point H2SO4 (10 drops) was added. After an additional 18 h, the reaction mixture was cooled to rt, poured into saturated aqueous NaHCO3 and extracted with EtOAc. The extract was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow-white solid (5.19 g, 96%).

Workup

  1. customTho reaction mixture
  2. temperatureat reflux for 18 hours
  3. stirringThe reaction mixture was stirred
  4. additionwas added
  5. extractionextracted with EtOAc
  6. dry with materialThe extract was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e4746020cc9485b805c1f35fb1f99ff
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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