Potassium Carbonate → 2-(3-Hexanoylphenoxy)methyl naphthalene

HRID 868435Notes

Reaction equation

HRID 868435 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C:13]([C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)(=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[C:13]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)(=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 143491261-(3-Hydroxyphenyl)hexan-1-one

Product 1

HCID 142577882-(3-Hexanoylphenoxy)methyl naphthaleneYield 57.9%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture containing 2-bromomethyl naphthalene (3.0 g, 13.5 mmol), 3-hexanoylphenol (2.6 g, 13.5 mmol), powdered potassium carbonate (19.0 g, 135 mmol) and potassium iodide (0.1 g) in dry acetone (100 ml) was refluxed for two days. Most of the solvent was removed after filtering off the solid residue. The oil was purified by chromatography on silica gel using a 5% ethylacetate in hexane solution as eluent to leave the desined product as a clear, colorless liquid (2.6 g).

Workup

  1. temperaturewas refluxed for two days
  2. customMost of the solvent was removed
  3. filtrationafter filtering off the solid residue
  4. customThe oil was purified by chromatography on silica gel using a 5% ethylacetate in hexane solution as eluent

Sources & evidence

ORD record
ord-a691940918ea45fdb65c64c00b5114fd
Source dataset
uspto-grants-1988_10
Patent number
US04778931

Reaction notes

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