Methyl Chloride → 6-Benzoyl-(6H)-dibenz[c,e][1,2]oxaphosphorin 6-oxide

HRID 1085359Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:11][P:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]2[CH:22]=[CH:23][CH:24]=[CH:25][C:14]=2[O:13]1.CCl>C1(C)C=CC=CC=1>[C:1]([P:12]1(=[O:11])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]2[CH:22]=[CH:23][CH:24]=[CH:25][C:14]=2[O:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

56 g (0.399 mol) of benzoyl chloride were warmed to 80° to 85° C. under a nitrogen atmosphere. 92 g (0.4 mol) of 6-methoxy-(6H)-dibenz[c,e][1,2]oxaphosphorin were added dropwise over the course of 90 minutes while stirring. The temperature was then increased in steps to 130° C. It was kept at this temperature until evolution of methyl chloride could no longer be detected. The residue was digested with 70 ml of toluene at room temperature. 116 g (90% of theory) of the abovementioned compound, which, after rapid recrystallization from ethanol, had a melting point of 134° to 135° C.

Workup

custom116 g (90% of theory) of the abovementioned compound, which, after rapid recrystallization from ethanol

Sources & evidence

ORD record: ord-89013759b44e43e2b1e5772b45afc206
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05008426

Reaction notes

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