Phosphorus trichloride → HCID 10665599, compound

HRID 1584530Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([C:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=2)[C:6]=1[OH:21])([CH3:4])([CH3:3])[CH3:2].[P:22](Cl)(Cl)[Cl:23]>>[C:11]([C:9]1[CH:8]=[C:7]2[C:6](=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:10]=1)[O:21][P:22]([Cl:23])[C:16]1[CH2:17][CH2:18][CH2:19][CH2:20][C:15]2=1)([CH3:14])([CH3:13])[CH3:12]

Participants

Reactant 2

HCID 24387Phosphorus trichloride

HCID 10541232HCID 10541232, compound2×

Product 1

HCID 10665599HCID 10665599, compoundYield 88%

Procedure

A mixture consisting of 28.7 g (0.10 mol) of 2,4-di-tert-butyl-6-cyclohexen-1-yl-phenol (compound 102, Example 1b) and 17.5 ml (0.20 mol) of phosphorus trichloride is refluxed under nitrogen for 5 hours. Excess phosphorus trichloride is removed by distillation and the residue is then distilled under vacuum at 165-167° C./0.01 mbar, giving 30.8 g (88%) of 6,8-di-tert-butyl-10-chloro-2,3,4,10-tetrahydro-l H-9-oxa-10-phosphaphenanthrene, a colourless thick liquid which slowly crystallises when standing; 31P--NMR (CDCl3): δ=130.5 ppm (s); 1H--NMR (CDCl3): δ(ppm): 1.34 (s, 9H, (CH3)3C--), 1.44 (s, 9H, (CH3)3C--), (compound (202), Table 2).

Workup

temperatureis refluxed under nitrogen for 5 hours
customExcess phosphorus trichloride is removed by distillation
distillationthe residue is then distilled under vacuum at 165-167° C./0.01 mbar

Sources & evidence

ORD record: ord-7f5610ed467a484b828d1afb014bd547
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932642

Reaction notes

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