Chloroacetonitrile → HCID 21830913, compound

HRID 2257022Notes

Reaction equation

HRID 2257022 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:16][C:17]#[N:18]>CN(C=O)C>[C:17]([CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)#[N:18]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 21830913HCID 21830913, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of methyl 4-hydroxyphenylacetate (10 g, 0.06 mol) in DMF (100 ml) was added to 97% NaH (1.78 g, 0.072 mol) in DMF (60 ml) in an ice bath. The reaction mixture was stirred for 0.5 hours and then chloroacetonitrile (5.44 g, 0.072 mol) in DMF (50 ml) was added. The reaction mixture was stirred at room temperature for about 2 days, the solvent was removed in vacuo, and the residue was partitioned between water and ether. The organic layer was separated, washed with saturated Na2CO3 and then brine, and then was dried over MgSO4, filtered and concentrated in vacuo to afford 12.2 g of methyl 4-(cyanomethoxy)phenylacetate.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for about 2 days
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between water and ether
  4. customThe organic layer was separated
  5. washwashed with saturated Na2CO3
  6. dry with materialbrine, and then was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02eba92fc2844217b628328a1609c647
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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