Styrene → Benzene, ethenyl-, polymer with 1,3-butadiene

HRID 1816858Notes

Reaction equation

HRID 1816858 reaction equation
[CH2:1]=[CH:2][C:3]1C=CC=C[CH:4]=1.C=CC=C.O1CCCC1CCC.C([Li])CCC.C(C1C=C2C3=C4C(C=CC=C4C=C2)=CC=C3C=1C)[CH:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCOCC>CCCCCC>[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 7501StyreneHCID 78451,3-ButadieneHCID 5512402-Propyl tetrahydrofuraneHCID 86620807HCID 86620807, compoundHCID 178418339Butyllithium

Product 1

HCID 62697Benzene, ethenyl-, polymer with 1,3-butadiene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
23 °C

Procedure

To a 10 oz. nitrogen purged bottle, hexane (20 mL), styrene (1 gr, 30% in hexane), butadiene (5 gr, 20% in hexane), oligomeric oxolanyl propane (OOPs) (0.03 mL, 1.6M solution) and butyl lithium (0.1 mL, 1.54M) would be added. The bottle would be placed into 80° C. water bath for 10 minutes. After cooling to 23° C., a charge of cinnamyl-1-methylpyrene ether (10 mL, 0.14M in cyclohexane) would be added into the bottle. After continual cooling for 5 minutes, a charge of DVB (0.5 mL) would be added to the mixture. The reaction would proceed for 1 hour, and then would be terminated by adding isopropanol 0.1 mL).

Workup

  1. customwould be placed into 80° C.
  2. customfor 10 minutes
  3. additionwould be added into the bottle
  4. temperatureAfter continual cooling for 5 minutes
  5. additiona charge of DVB (0.5 mL)
  6. additionwould be added to the mixture
  7. customThe reaction
  8. customwould be terminated
  9. additionby adding isopropanol 0.1 mL)

Sources & evidence

ORD record
ord-9ceeedac92be4b4baee7f270202513ea
Source dataset
uspto-grants-2009_10
Patent number
US07597959B2

Reaction notes

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