Phenylacetyl chloride → HCID 22449363, compound

HRID 487262Notes

Reaction equation

HRID 487262 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].[C:8]1([CH2:14][C:15](Cl)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[OH:16][C:15](=[C:4]([C:3]#[N:7])[C:5]#[N:6])[CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8010MalononitrileHCID 24758Sodium hydride

Product 1

HCID 22449363HCID 22449363, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 60% NaH/mineral oil dispersion (3.2 g, 79.5 mmol) in THF (100 ml) at room temperature under argon was added dropwise malononitrile (5.0 ml, 79.5 mmol) in THF (20 ml) over 30 minutes. The reaction mixture was stirred at room temperature for 30 minutes, then phenylacetyl chloride (10.5 ml, 79.5 mmol) in THF (10 ml) was added dropwise over 10 minutes. The reaction mixture was stirred at room temperature for 1.5 hours, the solvent was removed in vacuo, and the residue was partitioned between ether and 2N H2SO4. The ether layer was separated, washed with water, dried over anhydrous MgSO4, filtered through a silica gel plug and the solvent was removed in vacuo to afford 13.8 g (94%) of (1-hydroxy-2-phenylethylidene)malononitrile as an amber oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1.5 hours
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between ether and 2N H2SO4
  4. customThe ether layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered through a silica gel plug
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fbc354bd0acb4e8c8168227576fe57fa
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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