Bromodiphenylmethane → HCID 19026043, compound

HRID 507720Notes

Reaction equation

HRID 507720 reaction equation
C1(C(C2C=CC=CC=2)O[P:9]2[O:14][CH2:13][C:12]3([CH2:19][O:18][P:17](OC(C4C=CC=CC=4)C4C=CC=CC=4)[O:16][CH2:15]3)[CH2:11][O:10]2)C=CC=CC=1.C1(C(Br)C2C=CC=CC=2)C=CC=CC=1>>[CH2:19]1[C:12]2([CH2:11][O:10][PH:9][O:14][CH2:13]2)[CH2:15][O:16][PH:17][O:18]1

Participants

3

Reactant 2

HCID 236603BromodiphenylmethaneHCID 22015088HCID 22015088, compound

Product 1

HCID 19026043HCID 19026043, compoundYield 203%

Procedure

560.5 g (1.0 mol) of 3,9-bis(diphenylmethoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecane and 494.3 g (2.0 mol) of diphenylmethyl bromide were charged into a reactor equipped with a stirrer, thermometer and capacitor, and dry nitrogen was caused to flow into the reactor under agitation at room temperature. Thereafter, heating was started with an oil bath which was kept at 150° C. for 15 minutes. The oil bath was removed to cool the reactor to room temperature. 2,000 ml of acetone was added to the obtained reaction product which was a white solid and stirred to clean the reaction product, and the white powder was separated by filtration with a glass filter. Then, the separated white powder was cleaned with 2,000 ml of a 50 wt % aqueous solution of methanol and dried at 100 Pa and 120° C. for 8 hours to produce 398.0 g of 2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecane, 3,9-bis(diphenylmethyl)-3,9-dioxide. It was confirmed from mass spectral analysis, 1H, 31P nuclear magnetic resonance spectral analysis and elemental analysis that the product was 2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecane, 3,9-bis(diphenylmethyl)-3,9-dioxide. This compound had a yield of 71%, an HPLC purity of 99.1% and an acid value of 0.39 mgKOH/g.

Workup

  1. customequipped with a stirrer
  2. customto flow into the reactor under agitation at room temperature
  3. temperatureThereafter, heating
  4. customwas started with an oil bath
  5. customThe oil bath was removed
  6. addition2,000 ml of acetone was added to the obtained reaction product which
  7. customthe white powder was separated by filtration with a glass
  8. filtrationfilter
  9. customdried at 100 Pa and 120° C. for 8 hours

Sources & evidence

ORD record
ord-80c30355beea455ca5e5125af3985504
Source dataset
uspto-grants-2010_08
Patent number
US07786197B2

Reaction notes

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