Sodium hydride → HCID 15662563, compound

HRID 1073427Notes

Reaction equation

HRID 1073427 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:15])=[CH:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl[CH:17]([CH3:20])[C:18]#[N:19]>CN(C=O)C>[CH3:3][C:4]([CH3:15])=[CH:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:17]([CH3:20])[C:18]#[N:19])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5192252-ChloropropionitrileHCID 11435274HCID 11435274, compound

Product 1

HCID 15662563HCID 15662563, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

To NaH (0.246 g, 10.2 mmol) in 10 ml of DMF at 20° is added 4-(3-methyl-2-butenoxy)phenol (1.33 g, 10.2 mmol) in 5 ml of DMF. After anion formation is complete, the reaction is cooled to 5° C. and 2-chloropropionitrile (1.095 g, 12.2 mmol) is added gradually. Then, the reaction mixture is warmed to RT and heated at 45° for 18 hrs. The reaction is cooled to RT, poured into ice water and extracted with ether. The combined organic layers are washed with 10% NaOH, followed with water until neutral, and with brine, and dried over calcium sulfate. Ether is removed under vacuum to give 2-[4-(3-methyl-2-butenoxy)phenoxy]propionitrile.

Workup

  1. temperatureThen, the reaction mixture is warmed to RT
  2. temperatureheated at 45° for 18 hrs
  3. temperatureThe reaction is cooled to RT
  4. extractionextracted with ether
  5. washThe combined organic layers are washed with 10% NaOH
  6. dry with materialdried over calcium sulfate
  7. customEther is removed under vacuum

Sources & evidence

ORD record
ord-88c8b280a49147a88fd55fd9cc56d09a
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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