Methanol → Benzaldehyde, 2-chloro-3,4-dihydroxy-5-nitro-

HRID 274486Notes

Reaction equation

HRID 274486 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[C:8]([O:11]C)[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][C:3]=1[CH:4]=[O:5].B(Br)(Br)Br.CO>C(Cl)Cl>[Cl:1][C:2]1[C:9]([OH:10])=[C:8]([OH:11])[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 144509952-Chloro-3-hydroxy-5-nitro-p-anisaldehyde

Product 1

HCID 5747986Benzaldehyde, 2-chloro-3,4-dihydroxy-5-nitro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.3 g of 2-chloro-3-hydroxy-5-nitro-p-anisaldehyde are dissolved in 80 ml of methylene chloride, treated with 0.82 ml of boron tribromide, stirred at 23° for 18 hours, the reaction mixture is treated with 5 ml of methanol while cooling with ice, evaporated, the residue is dried in a high vacuum, digested in water, filtered and recrystallized from acetonitrile. There is obtained 2-chloro-3,4-dihydroxy-5-nitrobenzaldehyde of m.p. 193°-195°.

Workup

  1. temperaturewhile cooling with ice
  2. customevaporated
  3. customthe residue is dried in a high vacuum
  4. filtrationfiltered
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-f761177a2c8f4d64bdb6a440d1a4afc6
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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