Allyl bromide → Ethyl 7-allyloxynaphthalene-2-carboxylate

HRID 463328Notes

Reaction equation

HRID 463328 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>[I-].[K+].CC(C)=O>[CH2:25]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1)[CH:24]=[CH2:23]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 12635629Ethyl 7-hydroxynaphthalene-2-carboxylate

Product 1

HCID 20282953Ethyl 7-allyloxynaphthalene-2-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of ethyl 7-hydroxynaphthalene-2-carboxylate (37.5 g), anhydrous potassium carbonate (24.0 g), potassium iodide (0.5 g), and allyl bromide (29.0 g) was heated in refluxing acetone (200 ml) with stirring for 15 hours. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in ethyl-acetate, washed with 2% sodium hydroxide solution and water, dried and evaporated to give a solid. Crystallisation from petroleum ether (b.p. 40-60) afforded ethyl 7-allyloxynaphthalene-2-carboxylate (36 g), m.p. 60°-61°.

Workup

  1. temperaturewas heated
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in ethyl-acetate
  5. washwashed with 2% sodium hydroxide solution and water
  6. customdried
  7. customevaporated
  8. customto give a solid
  9. customCrystallisation from petroleum ether (b.p. 40-60)

Sources & evidence

ORD record
ord-010ec888aa54404db7f6eec6f76e531c
Source dataset
uspto-grants-1985_05
Patent number
US04518612

Reaction notes

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