Benzene → Lauryl Methacrylate

HRID 1451137Notes

Reaction equation

HRID 1451137 reaction equation
[Na].CC(C1C=CC=CC=1)=C.C1C=CC=CC=1.C1(C([Li])(C2C=CC=CC=2)CCCCC)C=CC=CC=1.[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][O:48][C:49]([C:51]([CH3:53])=[CH2:52])=[O:50].Cl.C[OH:56]>O1CCCC1>[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][O:48][C:49]([C:51]([CH3:53])=[CH2:52])=[O:50].[CH3:53][C:51]([C:49]([O:48][CH2:47][CH2:46][OH:56])=[O:50])=[CH2:52]

Participants

10

Reactant 7

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 887MethanolHCID 7407Alpha-MethylstyreneHCID 8906Lauryl MethacrylateHCID 5360545SodiumHCID 178506801HCID 178506801, compound

Product 2

HCID 8906Lauryl MethacrylateHCID 133602-Hydroxyethyl Methacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

Under a high vacuum, a tetarahydrofuran solution of sodium salt of a-methylstyrene tetramer was introduced into a polymerization vessel, and removed after sufficiently washing the vessel. Then, 198 ml of tetrahydrofuran and 18 ml (3.0 mmole) of a benzene solution of 1,1-diphenylhexyl lithium were introduced under the room temperature into the vessel, which in turn was cooled to -78° C. Then, 111 ml (74 mmole) of a tetrahydrofuran solution of n-lauryl methacrylate was introduced into the vessel to start polymerization. After a lapse of 2 hours, the mixture was further stirred for 30 minutes with introduction of 95 ml (66 mmole) of a tetrahydrofuran solution of 3-methacryloylethoxydimethylisopropylsilane, thereafter the reaction was stopped with addition of 2 ml of methanol, and 1 ml of 2N-hydrochloric acid was added into the reaction vessel to obtain a block polymer of poly n-lauryl methacrylate and polyhydroxyethyl methacrylate. After the reaction was finished, the solvent was removed so that the nonvolatile content was 50%. Hydrophobic and hydrophilic blocks forming this block polymer exhibited molecular weights of 2410 and 1210 respectively.

Workup

  1. customremoved
  2. washafter sufficiently washing the vessel
  3. custompolymerization
  4. additionwas added into the reaction vessel

Sources & evidence

ORD record
ord-a7e790b7600a4e25951ef7cdaee697c8
Source dataset
uspto-grants-1997_02
Patent number
US05603986

Reaction notes

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