Ethyl 8-allyl-7-hydroxynaphthalene-2-carboxylate → Ethyl 7-hydroxy-8-propylnaphthalene-2-carboxylate

HRID 463330Notes

Reaction equation

HRID 463330 reaction equation
[CH2:1]([C:4]1[C:5]([OH:19])=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:9]2)[CH:2]=[CH2:3]>C(O)C.[Pd]>[OH:19][C:5]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 1

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

Product 1

HCID 20282955Ethyl 7-hydroxy-8-propylnaphthalene-2-carboxylateYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 8-allyl-7-hydroxynaphthalene-2-carboxylate (4 g) in ethanol was hydrogenated at 3 atmospheres in the presence of a 5% palladium charcoal catalyst for 1 hour. Filtration and evaporation of the filtrate gave a solid, which crystallised from benzene-petroleum ether (b.p. 60-80) to give ethyl 7-hydroxy-8-propylnaphthalene-2-carboxylate (3.2 g), m.p. 114°-115°.

Workup

  1. filtrationFiltration and evaporation of the filtrate
  2. customgave a solid, which
  3. customcrystallised from benzene-petroleum ether (b.p. 60-80)

Sources & evidence

ORD record
ord-19f1a84eaa4344539d6234e9f6d52d8e
Source dataset
uspto-grants-1985_05
Patent number
US04518612

Reaction notes

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