1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → 2,4,8,10-Tetra-tert-butyl-6-[1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yloxy]-dibenzo[d,g][1,3,2]dioxaphosphocin

HRID 1383029Notes

Reaction equation

HRID 1383029 reaction equation
[P:1](Cl)(Cl)Cl.[CH2:5]([C:21]1[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:24]=[C:23]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:22]=1[OH:35])[C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[C:8]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:7]=1[OH:20].C(N(CC)CC)C.[OH:43][CH:44]1[CH2:49][C:48]([CH3:51])([CH3:50])[N:47]([OH:52])[C:46]([CH3:54])([CH3:53])[CH2:45]1>C1(C)C=CC=CC=1>[C:27]([C:25]1[CH:24]=[C:23]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:22]2[O:35][P:1]([O:43][CH:44]3[CH2:49][C:48]([CH3:50])([CH3:51])[N:47]([OH:52])[C:46]([CH3:54])([CH3:53])[CH2:45]3)[O:20][C:7]3[C:8]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:9][C:10]([C:12]([CH3:15])([CH3:13])[CH3:14])=[CH:11][C:6]=3[CH2:5][C:21]=2[CH:26]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 8471Triethylamine2×HCID 24387Phosphorus trichlorideHCID 843912,2'-Methylenebis(4,6-di-tert-butylphenol)

Product 1

HCID 703887822,4,8,10-Tetra-tert-butyl-6-[1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yloxy]-dibenzo[d,g][1,3,2]dioxaphosphocin

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

In a flame-dried flask under nitrogen, 4.4 ml of phosphorous trichloride in 100 ml of dry toluene is treated with a solution of 21.27 grams of 2,2'-methylene-bis-(4,6-di-tert-butylphenol) and 13.9 ml of triethylamine in 80 ml of toluene at a temperature not exceeding 5° C. The reaction is stirred at ambient temperature for 12 hours and the suspension is cooled to 5° C. The mixture is treated with 8.61 grams of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 7 ml of triethylamine in 100 ml of dry toluene. After stirring the mixture at room temperature for 12 hours, the mixture is filtered and the filtrate concentrated under reduced pressure. The residue is crystallized from acetonitrile to give 17.0 grams of a pale red solid.

Workup

  1. customexceeding 5° C
  2. temperaturethe suspension is cooled to 5° C
  3. stirringAfter stirring the mixture at room temperature for 12 hours
  4. filtrationthe mixture is filtered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue is crystallized from acetonitrile

Sources & evidence

ORD record
ord-0f70962a89b44653991083be17a5ce8e
Source dataset
uspto-grants-1989_02
Patent number
US04808645

Reaction notes

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