N-methyl-2-pyrrolidone → 2,4,8,10-tetrakis(tert-butyl)-6-chloro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin

HRID 2259848Notes

Reaction equation

HRID 2259848 reaction equation
[CH2:1]([C:17]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]=1[OH:31])[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[OH:16].CN1CCCC1=O.[P:39](Cl)(Cl)[Cl:40]>C1(C)C=CC=CC=1>[Cl:40][P:39]1[O:16][C:3]2[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][C:6]([C:8]([CH3:11])([CH3:9])[CH3:10])=[CH:7][C:2]=2[CH2:1][C:17]2[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]=2[O:31]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 24387Phosphorus trichlorideHCID 843912,2'-Methylenebis(4,6-di-tert-butylphenol)

Product 1

HCID 128566622,4,8,10-tetrakis(tert-butyl)-6-chloro-12H-dibenzo[d,g][1,3,2]dioxaphosphocinYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 25.0 g (0.059 mol) of 2,2'-methylenebis(4,6-di-tert-butylphenol) and 0.57 mL (5.9 mmol) of 1-methyl-2-pyrrolidinone in 275 mL of toluene at ambient temperature is added dropwise 5.16 mL (0.059 mol) of phosphorus trichloride. After the addition is complete, the reaction mixture is refluxed for eight hours. After cooling the mixture to ambient temperature, the toluene is removed in vacuo and the reaction mass is re, crystallized twice from 250 mL of 98% acetonitrile and 2% toluene (% by volume) in acetonitrile. The recrystallization solvent is removed by decantation and the residue is dried under vacuum to give 21.4 g (79% yield) of the title compound as an off-white solid melting at 227°-230° C.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture is refluxed for eight hours
  3. customthe toluene is removed in vacuo
  4. customcrystallized twice from 250 mL of 98% acetonitrile and 2% toluene (% by volume) in acetonitrile
  5. customThe recrystallization solvent is removed by decantation
  6. customthe residue is dried under vacuum

Sources & evidence

ORD record
ord-5e94e94347d04d619ade0965dedda8da
Source dataset
uspto-grants-1995_12
Patent number
US05475042

Reaction notes

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