4-Cyanophenol → HCID 21701951, compound

HRID 1596480Notes

Reaction equation

HRID 1596480 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[Cl:12][CH2:13][C:14]([CH2:16]Cl)=[CH2:15]>COCCOC>[Cl:12][CH2:13][C:14](=[CH2:15])[CH2:16][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 130194-CyanophenolHCID 158593-Chloro-2-chloromethyl-1-propeneHCID 24758Sodium hydride

Product 1

HCID 21701951HCID 21701951, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 4-cyanophenol (11.9 g; 0.1 mol) in 1,2-dimethoxyethane (100 mL) was slowly added to a stirred and cooled (0° C.) suspension of NaH (4.0 g; 0.1 mol; 55% dispersion) in 1,2-dimethoxyethane (250 mL). The reaction mixture was refluxed for 1 hour and then allowed to cool to room temperature. 3-Chloro-2-chloromethyl-propene (20 g; 0.16 mol) was added in one portion and the reaction mixture was stirred at 45° C. for 40 hours. The reaction mixture was partitioned between DCM and NaHCO3 (satd.) and the organic layer collected, dried, concentrated and purified using column chromatography (DCM:MeOH; 50:1) to give the sub-title ompound in a 66% yield.

Workup

  1. temperaturecooled
  2. temperatureThe reaction mixture was refluxed for 1 hour
  3. stirringthe reaction mixture was stirred at 45° C. for 40 hours
  4. customThe reaction mixture was partitioned between DCM and NaHCO3 (satd.)
  5. customthe organic layer collected
  6. customdried
  7. concentrationconcentrated
  8. custompurified
  9. customto give the sub-title ompound in a 66% yield

Sources & evidence

ORD record
ord-6355f732372b42af9ba8beefc92551cd
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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