Hydrochloric Acid → 5-Benzoyl-2-nitrobenzaldehyde

HRID 390244Notes

Reaction equation

HRID 390244 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].Cl>CCl>[C:13]([C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([CH:5]=1)[CH:3]=[O:2])(=[O:14])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19816024[3-(Dimethoxymethyl)-4-nitrophenyl]phenylmethanone

Product 1

HCID 198160555-Benzoyl-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6327Methyl ChlorideSolvent

Procedure

A mixture of (3-dimethoxymethyl-4-nitro-phenyl)-phenyl-methanone (0.0659 mol) and 5N HCl (40 mL) in CH3Cl (80 mL) was stirred at room temperature overnight. Then the mixture was refluxed for 4 h. After cooling, the organic layer was separated. The organic layer was alkalized by adding dropwise NH4OH. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue (14.6 g) was crystallized from diisopropyl ether/EtOAc (50 mL:20 mL). The precipitate was filtered off, washed with diisopropyl ether/EtOAc, diisopropyl ether and dried in vacuo at 50° C. to yield the title compound as a residue.

Workup

  1. temperatureThen the mixture was refluxed for 4 h
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. additionby adding dropwise NH4OH
  5. washThe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue (14.6 g) was crystallized from diisopropyl ether/EtOAc (50 mL:20 mL)
  9. filtrationThe precipitate was filtered off
  10. washwashed with diisopropyl ether/EtOAc, diisopropyl ether
  11. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-b2f38c0dbe6d4b08a1b80c443b2dd8d8
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

Loading…