3,4-Dimethylbenzoyl chloride → 6-(3,4-Dimethylbenzoyl)-(6H)-dibenz[c,e][1,2]oxaphosphorin 6-oxide

HRID 2371986Notes

Reaction equation

HRID 2371986 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=[O:6].C[O:13][P:14]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]2[CH:24]=[CH:25][CH:26]=[CH:27][C:16]=2[O:15]1>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([P:14]1(=[O:13])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]2[CH:24]=[CH:25][CH:26]=[CH:27][C:16]=2[O:15]1)=[O:6]

Participants

3

Reactant 2

HCID 27585353,4-Dimethylbenzoyl chlorideHCID 114361486-methoxy-(6H)-dibenz[c,e][1,2]-oxaphosphorin

Product 1

HCID 143662846-(3,4-Dimethylbenzoyl)-(6H)-dibenz[c,e][1,2]oxaphosphorin 6-oxide

Conditions

Temperature
100 °C

Procedure

50.6 g (0.3 mol) of 3,4-dimethylbenzoyl chloride were warmed to 80° C. under a nitrogen atmosphere. 69 g (0.3 mol) of 6-methoxy-(6H)-dibenz[c,e][1,2]oxaphosphorin were added dropwise while stirring. Crystallization began even during the dropwise addition, and the temperature was therefore increased to 100° C.; at the same time, an additional 100 ml of toluene were added dropwise. When the dropwise addition was complete, the mixture was heated to reflux. When the reaction was complete and after crystallization, 87 g (83% of theory) of the abovementioned compound, which had a melting point of 160° to 162° C., were obtained.

Workup

  1. customCrystallization
  2. additionbegan even during the dropwise addition
  3. additionat the same time, an additional 100 ml of toluene were added dropwise
  4. additionWhen the dropwise addition
  5. temperaturethe mixture was heated to reflux
  6. customafter crystallization, 87 g (83% of theory) of the abovementioned compound, which
  7. customwere obtained

Sources & evidence

ORD record
ord-62bc07d2155b4ab68c2958717c98f57d
Source dataset
uspto-grants-1992_03
Patent number
US05096935

Reaction notes

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