Hydrochloric Acid → 5-Benzoyl-2-nitrobenzaldehyde

HRID 2247889Notes

Reaction equation

HRID 2247889 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>ClC(Cl)Cl>[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-nitrobenzaldehydeYield 49%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 19 parts of intermediate 10, namely [3-(dimethoxymethyl)-4-nitrophenyl]phenylmethanone, 40 parts of an aqueous hydrochloric acid solution 5N and 120 parts of trichloromethane was stirred overnight at room temperature and for 4 hours at reflux temperature. After cooling, the organic layer was separated, basified with NH4OH (aq.), washed with water, dried, filtered and evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and ethyl acetate. The product was filtered off, washed successively with a mixture of 2,2'-oxybispropane and ethyl acetate and with 2,2'-oxybispropane and dried in vacuo at 50° C., yielding 7.61 parts (49.0%) of 5-benzoyl-2-nitrobenzaldehyde; mp. 96.7° C. (interm. 11).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and ethyl acetate
  9. filtrationThe product was filtered off
  10. washwashed successively with a mixture of 2,2'-oxybispropane and ethyl acetate and with 2,2'-oxybispropane
  11. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-4bf2482f3751404f9424d61f803fe068
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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