Hydrochloric Acid → Ethyl 7-hydroxynaphthalene-2-carboxylate

HRID 2295413Notes

Reaction equation

HRID 2295413 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.Cl.[CH2:16](O)[CH3:17]>>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]([O:14][CH2:16][CH3:17])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 145125257-Hydroxy-2-naphthoic acid

Product 1

HCID 12635629Ethyl 7-hydroxynaphthalene-2-carboxylate

Procedure

A solution of 7-hydroxynaphthalene-2-carboxylic acid (56.09 g) in ethanol (200 ml) was saturated with dry hydrogen chloride and then refluxed for 30 minutes. The mixture was evaporated to about half volume, treated with water, and extracted with ethyl acetate, which was washed with water, and sodium bicarbonate solution, dried and evaporated to give a solid. Crystallisation from ethyl acetate afforded ethyl 7-hydroxynaphthalene-2-carboxylate (37.5 g), m.p. 155°-156°.

Workup

  1. temperaturerefluxed for 30 minutes
  2. customThe mixture was evaporated to about half volume
  3. additiontreated with water
  4. extractionextracted with ethyl acetate, which
  5. washwas washed with water, and sodium bicarbonate solution
  6. customdried
  7. customevaporated
  8. customto give a solid
  9. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-89b06af337364db2ae9652671b829b71
Source dataset
uspto-grants-1984_01
Patent number
US04424231

Reaction notes

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