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

HRID 1906963Notes

Reaction equation

HRID 1906963 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([N+:14]([O-])=[O:15])[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[Al]>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[N:14][OH:15])[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 5359268AluminumHCID 54289141Methyl 4-(2-nitropropen-1-yl)benzoate

Product 1

HCID 867397271-(4-Carbomethoxyphenyl)propan-2-one oximeYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Carbomethoxyphenyl)-2-nitroprop-1-ene (31.0 g) in tetrahydrofuran (900 ml) was stirred with aluminium amalgam, made in the usual way from aluminium (13.5 g) and mercuric chloride (6.9 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 (17.0 g). τ (CDCl3) 8.27 (3H, s), 6.22 (2H, s), 6.13 (3H, s), 2.63 (2H, d, J=8 Hz), 1.95 (2H, d, J=8 Hz).

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-bbf96c30a5dc4668a1be38495fbf7dba
Source dataset
uspto-grants-1987_03
Patent number
US04654371

Reaction notes

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