Phosphorus trichloride → HCID 20082255, compound

HRID 1609784Notes

Reaction equation

HRID 1609784 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH3:15])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[P:17]([Cl:20])(Cl)Cl>CN(C)C=O.C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH3:15])[C:6]=1[O:16][P:17]([Cl:20])[O:16][C:6]1[C:7]([CH3:15])=[CH:8][C:9]([C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24387Phosphorus trichlorideHCID 69224Phenol, 2,4-bis(1,1-dimethylethyl)-6-methyl-

Product 1

HCID 20082255HCID 20082255, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
50 °C

Procedure

890.3 g (4 mol) of 2,4-di-tert-butyl-6-methylphenol, 4.2 g of dimethylformamide and 170.0 g of xylene are introduced into a four-neck flask which has been flushed with nitrogen and is fitted with a thermometer, dropping funnel, reflux condenser and distillation attachment. 274.9 g (2 mol) of phosphorus trichloride are added dropwise with stirring over the course of 1.5 hours at a temperature of 50° C. The reaction mixture is warmed to 130° C. and refluxed at this temperature for 1 hour. The reaction mixture is kept at 120° C. for 1 hour under a vacuum of 0.15 bar. Xylene is subsequently removed by distillation under a greater vacuum. After the vacuum has been broken using nitrogen, 959.5 g (1.9 mol) of the title compound are obtained as supercooled, yellow-orange, clear melt.

Workup

  1. customhas been flushed with nitrogen
  2. customis fitted with a thermometer
  3. temperaturereflux condenser
  4. distillationdistillation attachment
  5. temperatureThe reaction mixture is warmed to 130° C.
  6. temperaturerefluxed at this temperature for 1 hour
  7. waitThe reaction mixture is kept at 120° C. for 1 hour under a vacuum of 0.15 bar
  8. customXylene is subsequently removed by distillation under a greater vacuum

Sources & evidence

ORD record
ord-fe8bb390e62742689ba7acf0a2fca8fd
Source dataset
uspto-grants-1995_03
Patent number
US05401845

Reaction notes

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