Hydrochloric Acid → Ethyl 8-allyl-7-hydroxynaphthalene-2-carboxylate

HRID 2295415Notes

Reaction equation

HRID 2295415 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12]2)=[CH:7][CH:6]=1)C=C.C(N(CC)[C:23]1[CH:28]=CC=C[CH:24]=1)C.Cl>>[CH2:28]([C:14]1[C:5]([OH:4])=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:10]=[CH:9]2)[CH:23]=[CH2:24]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7061N,N-DiethylanilineHCID 20282953Ethyl 7-allyloxynaphthalene-2-carboxylate

Product 1

HCID 20282937Ethyl 8-allyl-7-hydroxynaphthalene-2-carboxylate

Procedure

Ethyl 7-allyloxynaphthalene-2-carboxylate (6.2 g) was heated in refluxing N,N-diethylaniline for 2 hours. The solution was cooled, treated with dilute hydrochloric acid and extracted with ethyl acetate, which was then washed with dilute hydrochloric acid, and water, dried and evaporated to a solid. Crystallisation from benzene/petroleum ether (b.p. 40-60) afforded ethyl 8-allyl-7-hydroxynaphthalene-2-carboxylate (4.5 g), m.p. 115°-116°.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with ethyl acetate, which
  3. washwas then washed with dilute hydrochloric acid, and water
  4. customdried
  5. customevaporated to a solid
  6. customCrystallisation from benzene/petroleum ether (b.p. 40-60)

Sources & evidence

ORD record
ord-9bebc23296dd4ed1ade55e2e89c20f7e
Source dataset
uspto-grants-1984_01
Patent number
US04424231

Reaction notes

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