Phenethyl bromide → HCID 19026043, compound

HRID 507719Notes

Reaction equation

HRID 507719 reaction equation
C1(CCO[P:10]2[O:15][CH2:14][C:13]3([CH2:20][O:19][P:18](OCCC4C=CC=CC=4)[O:17][CH2:16]3)[CH2:12][O:11]2)C=CC=CC=1.C1(CCBr)C=CC=CC=1>>[CH2:20]1[C:13]2([CH2:12][O:11][PH:10][O:15][CH2:14]2)[CH2:16][O:17][PH:18][O:19]1

Participants

3

Reactant 2

HCID 7666Phenethyl bromideHCID 11604517HCID 11604517, compound

Product 1

HCID 19026043HCID 19026043, compoundYield 184.8%

Procedure

436.4 g (1.0 mol) of 3,9-di(2-phenylethoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecane and 370.1 g (2.0 mol) of 2-phenylethyl 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 180° C. for 10 hours. The oil bath was removed to cool the reactor to room temperature. 2,000 ml of methanol 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 362.3 g of 2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecane, 3,9-di (2-phenylethyl)-3,9-dioxide. It was confirmed from mass spectral analysis, 1H, 31P nuclear magnetic resonance spectral analysis and elemental analysis that the product was bis-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecane, 3,9-di(2-phenylethyl)-3,9-dioxide. This compound had a yield of 83%, an HPLC purity of 99.3% and an acid value of 0.41 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 methanol 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-71f1dbebcaf94be19a4c5475d811c29a
Source dataset
uspto-grants-2010_08
Patent number
US07786197B2

Reaction notes

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