Triethylamine → 2,4,8,10-Tetra-tert-butyl-6-chlorodibenzo[d,f][1,3,2]dioxaphosphepine

HRID 1577494Notes

Reaction equation

HRID 1577494 reaction equation
[P:1]([Cl:4])(Cl)Cl.[C:5]([C:9]1[CH:10]=[C:11]([C:20]2[C:21]([OH:34])=[C:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:23]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:25]=2)[C:12]([OH:19])=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:14]=1)([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>C1(C)C=CC=CC=1>[P:1]1([Cl:4])[O:34][C:21]2[C:22]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:23][C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:25][C:20]=2[C:11]2[CH:10]=[C:9]([C:5]([CH3:6])([CH3:7])[CH3:8])[CH:14]=[C:13]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:12]=2[O:19]1

Participants

5

Reactant 3

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

Product 1

HCID 109836102,4,8,10-Tetra-tert-butyl-6-chlorodibenzo[d,f][1,3,2]dioxaphosphepine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

45.21 grams of phosphorous trichloride in 50 ml of toluene was added dropwise over 85 minutes to a solution of 123.0 grams of 4,4',6,6'-tetra-tert.-butyl-2,2'-biphenol and 60.6 grams of triethylamine in about 600 ml of toluene and stirred at room temperature overnight (about 20 hours). The reaction product was filtered free of triethylamine hydrochloride, the desired product being isolated by removal of the solvent at reduced pressure to yield a solid m.p. 168°-174°.

Workup

  1. filtrationThe reaction product was filtered free of triethylamine hydrochloride

Sources & evidence

ORD record
ord-18f386962f3e419ea2d3cbfe5b5568ef
Source dataset
uspto-grants-1981_09
Patent number
US04288391

Reaction notes

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