Aluminum → 1-(4-Carbomethoxymethoxyphenyl)propan-2-one oxime

HRID 1758986Notes

Reaction equation

HRID 1758986 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]([N+:16]([O-])=[O:17])[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2].[Al]>O1CCCC1>[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=[N:16][OH:17])[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 5359268AluminumHCID 536833001-(4-Carbomethoxymethoxyphenyl)-2-nitroprop-1-ene

Product 1

HCID 867384661-(4-Carbomethoxymethoxyphenyl)propan-2-one oximeYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Carbomethoxymethoxyphenyl)-2-nitroprop-1-ene (8.7 g) in tetrahydrofuran (100 ml) was stirred with aluminium amalgam, made in the normal way from aluminium (6 g) and mercuric chloride (3 g). The mixture was cooled in ice and stirring was continued until reaction was complete. The slurry was filtered through celite and the filtrate was evaporated to give a cream solid (7.5 g). τ(CDCl3) 8.24 (3H, s), 6.36 (2H, s), 6.24 (3H, s), 5.43 (2H, s), 3.20 (2H, d, J=8 Hz), 2.83 (2H, d, J=8 Hz), 2.5-3.4 (1H, broad, disappears with D2O).

Workup

  1. temperatureThe mixture was cooled in ice
  2. customwas continued until reaction
  3. filtrationThe slurry was filtered through celite
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-7a4d1c95e1084822b89c2c3fb88331ac
Source dataset
uspto-grants-1982_07
Patent number
US04338333

Reaction notes

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