1-Naphthol → Ethyl [(naphthalen-1-yl)oxy]acetate

HRID 1701712Notes

Reaction equation

HRID 1701712 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:1]1([O:11][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 1482829Ethyl [(naphthalen-1-yl)oxy]acetateYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

432 g 1-naphthol, 602 g ethyl 2-bromoacetate, 276 g potassium carbonate and 2.160 l. ethanol are refluxed for 18 hours, the precipitate filtered, the solvent evaporated under reduced pressure and the residue recrystallized from petroleum ether. The ester, which melts at 52° C., is obtained with an 80% yield.

Workup

  1. filtrationthe precipitate filtered
  2. customthe solvent evaporated under reduced pressure
  3. customthe residue recrystallized from petroleum ether

Sources & evidence

ORD record
ord-21a12086ad464ca88def1551028c3a16
Source dataset
uspto-grants-1980_03
Patent number
US04195093

Reaction notes

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