Acetic Acid → Ethyl 1,4-dihydroxynaphthalene-2-carboxylate

HRID 980122Notes

Reaction equation

HRID 980122 reaction equation
[O:1]([C:8]([C:10]1[CH:19]=[C:18]([OH:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[OH:21])=[O:9])[C:2]1C=CC=C[CH:3]=1.CC[O-].[Na+].C(O)(=O)C>C(O)C>[CH2:2]([O:1][C:8]([C:10]1[CH:19]=[C:18]([OH:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[OH:21])=[O:9])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6042492-Naphthalenecarboxylic acid, 1,4-dihydroxy-, phenyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 12388086Ethyl 1,4-dihydroxynaphthalene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

28 g of 2-phenoxycarbonyl-1,4-dihydroxynaphthalene was dissolved in ethanol under a nitrogen stream, and 20.4 g of sodium ethylate was added thereto, followed by refluxing for 5 hours under heating. After being cooled, the solution was made weakly acidic with acetic acid, then ethanol was distilled off. Ethyl acetate and water were added thereto to separate and extract the product. The product was purified through silica gel column chromatography with an element having the same composition as that used in the Synthesis Example 1 to obtain compound (6) as crytals. Yield: 13 g (56%).

Workup

  1. additionwas added
  2. temperatureby refluxing for 5 hours
  3. temperatureunder heating
  4. temperatureAfter being cooled
  5. distillationethanol was distilled off
  6. additionEthyl acetate and water were added
  7. customto separate
  8. extractionextract the product
  9. customThe product was purified through silica gel column chromatography with an element
  10. customthat used in the Synthesis Example 1

Sources & evidence

ORD record
ord-33f842f66bb74f2aa01e9a5fa2a63fb6
Source dataset
uspto-grants-1987_01
Patent number
US04636456

Reaction notes

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