alpha,alpha'-Dichloro-p-xylene → Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester

HRID 2373137

Reaction equation

HRID 2373137 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Cl)=[CH:5][CH:4]=1.[P:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12]CC>>[C:6]1([CH2:9][P:11](=[O:12])([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20])[CH:7]=[CH:8][C:3]([CH2:2][P:11](=[O:12])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 31215Triethyl phosphite

Product 1

HCID 78303Phosphonic acid, P,P'-(1,4-phenylenebis(methylene))bis-, P,P,P',P'-tetraethyl ester

Conditions

Temperature
180 °C

Procedure

A mixture of α,α′-dichloro-p-xylene (20 g, 0.114 mol) and triethyl phosphite (60 ml) was refluxed at 180° C. overnight. 80 ml of hexanes was added, and white crystals were formed immediately. Then the mixture was cooled at 0° C., and the product was collected, washed three times with 40 ml of hexanes and isolated in 94.4% (40.8 g) yield.

Workup

  1. customwhite crystals were formed immediately
  2. temperatureThen the mixture was cooled at 0° C.
  3. customthe product was collected
  4. washwashed three times with 40 ml of hexanes
  5. customisolated in 94.4% (40.8 g)
  6. customyield

Sources & evidence

ORD record
ord-06046a032b19462a939e55a60924d148
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Linked notes

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