1,3-Dihydroxynaphthalene → [(4-Hydroxy-2-naphthalenyl)oxy]acetic acid methyl ester

HRID 1719419Notes

Reaction equation

HRID 1719419 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CC(C)=O>[CH3:24][O:23][C:21](=[O:22])[CH2:20][O:12][C:4]1[CH:3]=[C:2]([OH:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 86011,3-DihydroxynaphthaleneHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 54367121[(4-Hydroxy-2-naphthalenyl)oxy]acetic acid methyl esterYield 19%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.5180 g of 1,3-dihydroxynaphthalene and 1.70 g of anhydrous potassium carbonate in 10 ml of anhydrous acetone was stirred at room temperature for 1 hour. Methyl bromoacetate (0.91 ml) was added and stirring at room temperature was continued for 50 hours. The solvent was removed in vacuo and the residue was acidified and extracted with ethyl acetate. The dried (magnesium sulfate) extract was concentrated in vacuo and the product was purified by high pressure liquid chromatography using 20% ethyl acetate-toluene to give 0.419 g (19% yield) of [(4-hydroxy-2-naphthalenyl)oxy]acetic acid methyl ester as an oil.

Workup

  1. stirringstirring at room temperature
  2. waitwas continued for 50 hours
  3. customThe solvent was removed in vacuo
  4. extractionextracted with ethyl acetate
  5. dry with materialThe dried (magnesium sulfate)
  6. extractionextract
  7. concentrationwas concentrated in vacuo
  8. customthe product was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-7db0530057b04222a5d4f5243c55694d
Source dataset
uspto-grants-1985_09
Patent number
US04539419

Reaction notes

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