Acetonitrile → 1-O-(2,4,8,10-Tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl)-2,2'-methylenebis-(4,6-di-tert-butylphenol)

HRID 487033

Reaction equation

HRID 487033 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].C(N(CC)CC)C.Cl[C:40]1[C:41]([C:67]([CH3:70])([CH3:69])[CH3:68])=[CH:42][C:43]2[C:49]3[CH:50]=[C:51]([C:58]([CH3:61])([CH3:60])[CH3:59])[CH:52]=[C:53]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:48]=3[O:47][PH:46][O:45][C:44]=2[C:62]=1[C:63]([CH3:66])([CH3:65])[CH3:64].C(#N)C>C1(C)C=CC=CC=1>[C:58]([C:51]1[CH:52]=[C:53]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:48]2[O:47][P:46]([O:31][C:18]3[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:22][C:17]=3[CH2:1][C:2]3[CH:7]=[C:6]([C:8]([CH3:11])([CH3:9])[CH3:10])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=3[OH:16])[O:45][C:44]3[C:62]([C:63]([CH3:65])([CH3:64])[CH3:66])=[CH:40][C:41]([C:67]([CH3:70])([CH3:69])[CH3:68])=[CH:42][C:43]=3[C:49]=2[CH:50]=1)([CH3:61])([CH3:60])[CH3:59]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 843912,2'-Methylenebis(4,6-di-tert-butylphenol)HCID 190964063-Chloro-2,4,8,10-tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepin

Product 1

HCID 190964071-O-(2,4,8,10-Tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl)-2,2'-methylenebis-(4,6-di-tert-butylphenol)Yield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a solution of 21.23 g (50 mmol) of 2,2'-methylenebis(4,6-di-tert-butylphenol) and 7 mL (50 mmol) of triethylamine in 200 mL of toluene is added dropwise a solution of 23.84 g (50 mmol) of 3-chloro-2,4,8,10-tetra-tert-butyl-dibenzo[d,f][1,3,2]dioxaphosphepin in 100 mL of toluene at ambient temperature. After 20 hours of stirring at ambient temperature, the reaction mass is filtered to remove triethylamine hydrochloride and the filtrate is concentrated in vacuo to give a brownish oil. Trituration of the crude oil with 200 mL of acetonitrile gives 36.65 g (85% yield) of a white solid: m.p.=195°-205° C.

Workup

  1. filtrationthe reaction mass is filtered
  2. customto remove triethylamine hydrochloride
  3. concentrationthe filtrate is concentrated in vacuo
  4. customto give a brownish oil

Sources & evidence

ORD record
ord-28a6dfbc7a7345e7821328838a35d828
Source dataset
uspto-grants-1994_03
Patent number
US05292785

Linked notes

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