Triphenylphosphine → 3-Formyl-2-hydroxy-5-nitrobenzyltriphenylphosphonium chloride

HRID 2254675Notes

Reaction equation

HRID 2254675 reaction equation
[Cl:1][CH2:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:5]([CH:6]=[O:7])[C:4]=1[OH:14].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1>[Cl-:1].[CH:6]([C:5]1[C:4]([OH:14])=[C:3]([CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=1)[CH2:2][P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:7]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 993803-(Chloromethyl)-2-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 867471163-Formyl-2-hydroxy-5-nitrobenzyltriphenylphosphonium chlorideYield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 4.53 g (20.9 mmoles) quantity of 3-chloromethyl-5-nitrosalicylaldehyde and 5.48 g (20.9 mmoles) of triphenylphosphine were dissolved in 30 ml of benzene and the solution obtained was refluxed with heating for 8 hours. After the reaction, the precipitate obtained was isolated by filtration, washed thoroughly with acetone and dried, giving 8.63 g (yield: 86%) of 3-formyl-2-hydroxy-5-nitrobenzyltriphenylphosphonium chloride as a yellow powder.

Workup

  1. customthe solution obtained
  2. temperaturewas refluxed
  3. temperaturewith heating for 8 hours
  4. customAfter the reaction
  5. customthe precipitate obtained
  6. customwas isolated by filtration
  7. washwashed thoroughly with acetone
  8. customdried

Sources & evidence

ORD record
ord-b91ef159c6d44bfc8d4a616a5245177d
Source dataset
uspto-grants-1993_08
Patent number
US05236958

Reaction notes

Loading…