Benzyl Bromide → HCID 22127020, compound

HRID 872023Notes

Reaction equation

HRID 872023 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:17]=1>C(#N)C.C(OCC)(=O)C>[CH2:7]([O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13080945Ethyl 4-hydroxynaphthalene-2-carboxylate

Product 1

HCID 22127020HCID 22127020, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (19.2 g) and benzyl bromide (19.0 g) were added to a solution of ethyl 4-hydroxy-2-naphthoate (20 g) in acetonitrile (200 ml) and the mixture was heated to reflux for 2 hours. After being cooled, the reaction solution was diluted with ethyl acetate and insoluble materials were filtered through Celite. The filtrate was concentrated in vacuo and the resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=100/1) to give ethyl 4-(benzyloxy)-2-naphthoate (27.8 g) as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter being cooled
  4. filtrationwere filtered through Celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=100/1)

Sources & evidence

ORD record
ord-36d45e44faa84bc589afe7bec1b08f06
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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