Dibutylamine → Dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine, N,N-dibutyl-2,4,8,10-tetrakis(1,1-dimethylethyl)-

HRID 128366Notes

Reaction equation

HRID 128366 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:17]([OH:30])=[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=2)[C:8]([OH:15])=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[P:31](Cl)(Cl)Cl.[CH2:35]([NH:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH3:38].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:22]([C:20]1[CH:19]=[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:17]2[O:30][P:31]([N:39]([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:35][CH2:36][CH2:37][CH3:38])[O:15][C:8]3[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][C:7]=3[C:16]=2[CH:21]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 8148DibutylamineHCID 8471TriethylamineHCID 24387Phosphorus trichlorideHCID 808083,3',5,5'-Tetrakis(1,1-dimethylethyl)(1,1'-biphenyl)-2,2'-diol

Product 1

HCID 20481433Dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine, N,N-dibutyl-2,4,8,10-tetrakis(1,1-dimethylethyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

170 g (0.414 mol) of 4,4',6,6'-tetra-tert-butyl-2,2'-biphenol in 150 ml of toluene is heated to 80°-90° C. in a nitrogen atmosphere, and 40 ml (0.458 mol) of phosphorus trichloride is added dropwise in the course of 2 hours. The reaction mixture is stirred at reflux temperature for 4 hours and, towards the end of the reaction, nitrogen gas is again introduced. There is then added dropwise at reflux temperature, during 11/2 hours, a solution of 53.5 g (0.414 mol) of dibutylamine and 41.9 g (0.414 mol) of triethylamine in 80 ml of toluene. After 15 hours, the reaction mixture is allowed to cool to room temperature, and the triethylamine hydrochloride which has precipitated is filtered off. The toluene is afterwards evaporated off, and the N-(2,4,8,10-tetra-tert-butyl-dibenz[d,f][1,3,2]dioxaphosphepin-6-yl)-dibutylamine obtained has a melting point of 140° C.

Workup

  1. additionis added dropwise in the course of 2 hours
  2. temperatureat reflux temperature for 4 hours
  3. customtowards the end of the reaction, nitrogen gas
  4. additionis again introduced
  5. additionThere is then added dropwise
  6. temperatureat reflux temperature
  7. custom2 hours
  8. customthe triethylamine hydrochloride which has precipitated
  9. filtrationis filtered off
  10. customThe toluene is afterwards evaporated off

Sources & evidence

ORD record
ord-79a7db922a534ba2add9c61c300cfdb6
Source dataset
uspto-grants-1981_03
Patent number
US04259492

Reaction notes

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