Methanol → 2-Chloro-4-nitrobenzaldehyde

HRID 399475Notes

Reaction equation

HRID 399475 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:13]=1[C:14](N(OC)C)=[O:15].CO>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:13]=1[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 18967570HCID 18967570, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2781662-Chloro-4-nitrobenzaldehydeYield 52.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Di-isobutylaluminium hydride (1.5M in toluene, 16.34 ml) was added to a stirred solution of 2-chloro-N-methoxy-N-methyl-4-nitrobenzamide (5 g) in toluene (100 ml) which had been cooled to -78° C. The mixture was stirred for 40 minutes. Methanol (10 ml) was added and the solvent was evaporated. The residue was partitioned between ethyl acetate and 2M aqueous hydrochloric acid. The organic solution was washed with water, dried (MgSO4) and evaporated to give 2-chloro-4-nitrobenzaldehyde (2 g).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between ethyl acetate and 2M aqueous hydrochloric acid
  3. washThe organic solution was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-e15476b67e3d46d4b96def7e1d217270
Source dataset
uspto-grants-1998_10
Patent number
US05821246

Reaction notes

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