Phenethyl bromide → HCID 19026043, compound

HRID 1917058Notes

Reaction equation

HRID 1917058 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 mole) of 3,9-di(2-phenylethoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane and 370.1 g (2.0 moles) of 2-phenylethyl bromide were charged into a reactor equipped with a stirrer, thermometer and condenser, and dry nitrogen was let flow into the reactor under agitation at room temperature. Then, heating was started with an oil bath, and the reactor was kept at an oil bath temperature of 180° C. for 10 hours. The oil bath was then removed to cool the reactor to room temperature. After 2,000 ml of methanol was added to the obtained white solid reaction product and stirred to wash the product, a white powder was separated by filtration with a glass filter. The obtained white powder and 4,000 ml of methanol were put into a reactor equipped with a condenser and stirrer and refluxed for about 2 hours. After cooling to room temperature, the crystal was separated by filtration and washed with 2,000 ml of methanol. The obtained white powder was dried at 100 Pa and 120° C. for 8 hours to obtain 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 by mass spectral analysis, 1Hand 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. The yield rate was 83%, the HPLC purity was 99.3%, and the acid value was 0.41 mgKOH/g.

Workup

  1. customequipped with a stirrer
  2. customat room temperature
  3. temperatureThen, heating
  4. customwas started with an oil bath
  5. customthe reactor was kept at an oil bath
  6. customThe oil bath was then removed
  7. additionAfter 2,000 ml of methanol was added to the obtained white solid reaction product
  8. washto wash the product
  9. customa white powder was separated by filtration with a glass
  10. filtrationfilter
  11. customThe obtained white powder and 4,000 ml of methanol were put into a reactor
  12. customequipped with a condenser and stirrer
  13. temperaturerefluxed for about 2 hours
  14. temperatureAfter cooling to room temperature
  15. customthe crystal was separated by filtration
  16. washwashed with 2,000 ml of methanol
  17. customThe obtained white powder was dried at 100 Pa and 120° C. for 8 hours

Sources & evidence

ORD record
ord-3f65354932d74cd0992f3cec561f785f
Source dataset
uspto-grants-2013_12
Patent number
US08618196B2

Reaction notes

Loading…