Sodium Methoxide → HCID 22494610, compound

HRID 1816686Notes

Reaction equation

HRID 1816686 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Br)=[CH:4][CH:3]=1.[CH3:16][O-:17].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:17][CH3:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 224947501-Bromo-4-((6-bromohexyl)oxy)benzene

Product 1

HCID 22494610HCID 22494610, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-bromo-4-(6-bromohexyloxy)benzene (6.0 g) and sodium methylate (28% in methanol) (10.3 ml) in methanol (30 ml) was stirred for 2 hours at 70° C. (bath temp.), and then the solvent was evaporated. The residue was neutralized by 1N-hydrochloric acid and extracted with ethyl acetate (100 ml), and washed with water and brine. The organic layer was dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude product. The crude product was purified by silica gel chromatography (20:1-10:1 hexane-ethyl acetate) to give 1-bromo-4-(6-methoxyhexyloxy)benzene (15.61 g) as a colorless oil.

Workup

  1. customthe solvent was evaporated
  2. extractionextracted with ethyl acetate (100 ml)
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationMagnesium sulfate was filtered off
  6. customthe filtrate was evaporated under reduced pressure
  7. customto give a crude product
  8. customThe crude product was purified by silica gel chromatography (20:1-10:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8409838ccddf4daba9392066aa636ba2
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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