Potassium Carbonate → HCID 22640879, compound

HRID 2415335Notes

Reaction equation

HRID 2415335 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:11])#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18]([CH:20]1[O:22][CH2:21]1)Br.O.CCOCC>CC(C)=O>[CH2:18]([O:11][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=1[C:1]#[N:2])[CH:20]1[O:22][CH2:21]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 12507070HCID 12507070, compoundHCID 21584184Diethylether water

Product 1

HCID 22640879HCID 22640879, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Cyano-3-methoxyphenol (1 g, 6.7 mmol) and powdered potassium carbonate (2.78 g, 20.1 mmol) were stirred in 15 mL of acetone for 5 minutes, followed by addition of epibromohydrin (1.38 g, 10.1 mmol). The mixture was stirred for 72 hours then poured into water/ether. The ether layer was separated, washed with sodium carbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The resulting crude solid was triturated with ether/hexane, filtered, and dried under vacuum to give 0.44 g of 2-cyano-3-methoxyphenyl glycidyl ether.

Workup

  1. customThe ether layer was separated
  2. washwashed with sodium carbonate and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude solid was triturated with ether/hexane
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-93060f2d6fb84e328b1d11d0352b7482
Source dataset
uspto-grants-2004_11
Patent number
US06818660B2

Reaction notes

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