Hydrochloric Acid → HCID 11833714, compound

HRID 1886202Notes

Reaction equation

HRID 1886202 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Mg].Br[C:9]1[CH:10]=[C:11]([CH3:16])[C:12]([CH3:15])=[CH:13][CH:14]=1.Cl[P:18](=[O:31])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(OCC)C.O1CCCC1>[C:19]1([P:18]([C:9]2[CH:10]=[C:11]([CH3:16])[C:12]([CH3:15])=[CH:13][CH:14]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:31])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 685044-Bromo-o-xyleneHCID 73910Diphenylphosphinic chlorideHCID 5462224MagnesiumHCID 21226445Aluminium lithium hydride

Product 1

HCID 11833714HCID 11833714, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A reaction vessel was charged with 100 ml of tetrahydrofuran (THF) which had been dried with lithium aluminum hydride, to which 2.83 g (0.1209 mol) of turning magnesium was added. With refluxing, a dried THF solution of 19.6 g (0.106 mol) of 4-bromo-o-xylene was added dropwise over one hour. After the completion of the addition, it was refluxed for about one hour and then cooled to 5° to 10° C. at which a dried THF solution of 25 g (0.106 mol) of chlorodiphenylphosphine oxide was added dropwise over about 3 hours. After the completion of the addition, it was mixed at 50° to 60° C. for 2 hours and allowed to stand for cooling. Then, 100 ml of dilute hydrochloric acid and 100 ml of diethyl ether were added to the resultant solution and mixed for 30 minutes. It was then extracted three time with 200 ml of diethyl ether. The extracted solution was rinsed three times with a 5% sodium hydrogencarbonate solution and dried with anhydrous sodium sulfate. The ether solution was condensed and subjected to column chromatography to obtain 25 g of white solid which had a chart (FIG. 1) of NMR spectrum in CDCl3 to find the following chemical structure; ##STR13##

Workup

  1. additionwas added
  2. temperatureWith refluxing
  3. additionAfter the completion of the addition, it
  4. temperaturewas refluxed for about one hour
  5. additionwas added dropwise over about 3 hours
  6. additionAfter the completion of the addition, it
  7. additionwas mixed at 50° to 60° C. for 2 hours
  8. temperaturefor cooling
  9. additionmixed for 30 minutes
  10. extractionIt was then extracted three time with 200 ml of diethyl ether
  11. washThe extracted solution was rinsed three times with a 5% sodium hydrogencarbonate solution
  12. dry with materialdried with anhydrous sodium sulfate
  13. customcondensed

Sources & evidence

ORD record
ord-a3d64127ccbc406684cc6aeb4a52c0d3
Source dataset
uspto-grants-1992_09
Patent number
US05149847

Reaction notes

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