Phenylacetonitrile → [3-(Dimethoxymethyl)-4-nitrophenyl]phenylmethanone

HRID 390243Notes

Reaction equation

HRID 390243 reaction equation
[C:1]1([CH2:7][C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C[O:13]CCOCCN(CCOCCOC)CCOCCOC.ClC1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[C:37]([CH:44]([O:47][CH3:48])[O:45][CH3:46])[CH:36]=1>CC(N(C)C)=O.CC(O)=O>[CH3:46][O:45][CH:44]([O:47][CH3:48])[C:37]1[CH:36]=[C:8]([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:13])[CH:40]=[CH:39][C:38]=1[N+:41]([O-:43])=[O:42]

Participants

7

Reactant 4

HCID 8794PhenylacetonitrileHCID 24758Sodium hydride2×HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzene

Product 1

HCID 19816024[3-(Dimethoxymethyl)-4-nitrophenyl]phenylmethanone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 31374DimethylacetamideSolvent2×

Procedure

Phenyl-acetonitrile (0.0793 mol) in DMA (100 ml) was stirred at room temperature and 50% NaH (0.0793 mol) was added portionwise. The mixture was stirred at room temperature until the evolution of H2 had ceased. TDA-1 (0.004 mol) was added and 4-chloro-2-dimethoxymethyl-1-nitro-benzene (0.0793 mol) in DMA (30 mL) was added dropwise. The mixture was stirred at 60° C. and at 100° C. overnight. 50% NaH (0.0793 mol) was added again and the mixture was stirred further at room temperature. The mixture was poured carefully on ice/water and brought to about pH 6-7 with CH3COOH. The product was extracted with CH2Cl2. The organic layer was dried (MgSO4) and evaporated. DMA was evaporated by use of high vacuum pump to yield the title compound as a residue.

Workup

  1. stirringThe mixture was stirred at 60° C. and at 100° C. overnight
  2. stirringthe mixture was stirred further at room temperature
  3. additionThe mixture was poured carefully on ice/water
  4. extractionThe product was extracted with CH2Cl2
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customDMA was evaporated by use of high vacuum pump

Sources & evidence

ORD record
ord-13ac6c6c91734cf2a058fbe93e4e951c
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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