O-Xylene → HCID 54151830, compound

HRID 481822Notes

Reaction equation

HRID 481822 reaction equation
Cl[P:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[O:3]1.[CH:16]([Mg]Br)([CH3:18])[CH3:17].[CH3:21][C:22]1C=CC=C[C:27]=1C>O1CCCC1>[CH:16]([P:2]([CH:22]([CH3:27])[CH3:21])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]1[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=1[OH:3])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 898166H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-HCID 178418365HCID 178418365, compound

Product 1

HCID 54151830HCID 54151830, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

46.9 g (0.2 mol) of 6-chloro-6H-dibenz[c,e][1,2]oxaphos-phorine in 250 ml of anhydrous o-xylene at 80° C. are introduced, in an argon atmosphere with stirring, and a solution of 0.45 mol of isopropylmagnesium bromide in 300 ml of tetrahydrofuran is added dropwise. Tetrahydrofuran is distilled off and the temperature slowly increased to 120° C. in the course of this. The mixture is then stirred for 3 hours at 120° C., cooled to room temperature and 100 ml of water are added. The mixture is neutralized with concentrated sulfuric acid, heated to 80° C. and the organic phase is separated off. During cooling, 51.7 g (90%) of colorless solid having melting point 82° to 84° C. crystallizes from the aqueous phase. 100 ml of 2N sodium hydroxide solution are added to this solid and the mixture is extracted with toluene. The toluene phase is separated off, washed with water, then dried with sodium sulfate and concentrated in vacuo. 38.9 g (68%) of colorless oil are obtained.

Workup

  1. distillationTetrahydrofuran is distilled off
  2. stirringThe mixture is then stirred for 3 hours at 120° C.
  3. temperaturecooled to room temperature
  4. addition100 ml of water are added
  5. temperatureheated to 80° C.
  6. customthe organic phase is separated off
  7. temperatureDuring cooling
  8. customcrystallizes from the aqueous phase
  9. addition100 ml of 2N sodium hydroxide solution are added to this solid
  10. extractionthe mixture is extracted with toluene
  11. customThe toluene phase is separated off
  12. washwashed with water
  13. dry with materialdried with sodium sulfate
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05327c64d7674f1b9125ff56e3977d9a
Source dataset
uspto-grants-1998_08
Patent number
US05789623

Reaction notes

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