Methanol → 4-Nitrosalicylic acid

HRID 1793632Notes

Reaction equation

HRID 1793632 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 757764-Nitro-o-anisic acid

Product 1

HCID 692664-Nitrosalicylic acidYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-4-nitro-benzoic acid (20 g, 0.102 mol) in 80 ml of CH2Cl2 at 0° C. was added BBr3 (1.0 M, 150 ml, 1.5 eq.). The resulting mixture was allowed to warm to rt and stirred for 2 h. MeOH was then added dropwise to quench the reaction at 0° C. and the volatile fraction was removed in vacuo. The residue was purified on a silica gel column with 6/4/0.3 of hexane, EtOAc and HOAc to give 18 g of 2-hydroxy-4-nitro-benzoic acid (M+: 183).

Workup

  1. customto quench
  2. customthe reaction at 0° C.
  3. customthe volatile fraction was removed in vacuo
  4. customThe residue was purified on a silica gel column with 6/4/0.3 of hexane, EtOAc and HOAc

Sources & evidence

ORD record
ord-cf1e71fe4c904007a09048112539d7b5
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

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