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

HRID 1429487Notes

Reaction equation

HRID 1429487 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+]>CC#N>[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 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of naphthalen-1-ol (196 mg, 1.35 mmol) in MeCN (5 mL) was added ethyl bromoacetate (269 mg, 1.62 mmol) and K2CO3 (372 mg, 2.70 mmol). The mixture was stirred at 80° C. for 4 hours. The mixture was filtered and the filtrate concentrated. The residue was used directly for the next step without further purification (300 mg, Yield 95%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was used directly for the next step without further purification (300 mg, Yield 95%)

Sources & evidence

ORD record
ord-ba07a930fe2c494fad392adae9fbbae7
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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