(1,1'-Biphenyl)-2-ol → 6H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-

HRID 1767182Notes

Reaction equation

HRID 1767182 reaction equation
[P:1]([Cl:4])(Cl)Cl.[C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[Cl-].[Zn+2].[Cl-]>[Cl:4][P:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17]1

Participants

4

Reactant 2

HCID 7017(1,1'-Biphenyl)-2-olHCID 24387Phosphorus trichloride

Product 1

HCID 898166H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

According to the present invention, the preparation of the arylphosphonite antioxidant is performed in an one-pot reactor. First of all, excessive phosphorous trichloride, 2-phenylphenol, and a trace amount of zinc chloride catalyst are put into the reactor and heated to proceed the first stage esterification and intramolecular cyclization reaction. The reaction temperature preferably between 30° C. and 200° C. The reaction equation of the esterification and cyclization are shown as the reaction equation (1). Whether the reaction is completed or not, it is determined by a 31P nuclear resonance spectroscopy. After the excessive phosphorous trichloride is recovered by vacuum distillation, the 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorin (CDOP) is obtained.

Workup

  1. customis performed in an one-pot reactor
  2. temperatureheated
  3. customthe first stage esterification and intramolecular cyclization reaction
  4. customThe reaction temperature preferably between 30° C. and 200° C
  5. distillationAfter the excessive phosphorous trichloride is recovered by vacuum distillation

Sources & evidence

ORD record
ord-866fe79e517a42f0b3a925df51b4d55b
Source dataset
uspto-grants-2007_06
Patent number
US07232922B2

Reaction notes

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