Benzyl Alcohol → Methyl methacrylate benzylmethacrylate

HRID 1071792Notes

Reaction equation

HRID 1071792 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCCCCCCCCCCCCC[CH2:26][O:27][C:28]([CH2:30][CH2:31]C1C=C(C(C)(C)C)[C:35]([OH:42])=[C:34]([C:43](C)(C)C)[CH:33]=1)=[O:29].CO>C1C2C(CCCC2)CCC1.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:28]([O:27][CH3:26])(=[O:29])[C:30]([CH3:31])=[CH2:1].[C:35]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:42])[C:34]([CH3:43])=[CH2:33]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 887MethanolHCID 16386Octadecyl DI-tert-butyl-4-hydroxyhydrocinnamate

Product 1

HCID 10333664Methyl methacrylate benzylmethacrylate

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 7044DecalinSolvent

Conditions

Temperature
185 °C

Procedure

350 grams (3.5 mole) of polymethylmethacrylate (Plexiglass VO 44 from Rohm & Haas), 378 grams of benzyl alcohol (3.5 mole) and 0.54 gram (0.1 mole %) of an antioxidant Irganox 1076 were heated to 180° C. to dissolve them in 550 cc of decalin. 13.86 grams of tetraisopropyl titanate was added and the temperature was maintained at 180-190° C. for 14 hours, and during this time 23 ml of distillate containing methanol was collected and the reaction was stopped. The polymer was precipitated in methanol then washed with hexane. After drying at 55° C. overnight in an vacuum oven, 404 gram of polymer were recovered with a DSC melting point of 93-94° C. NMR analysis showed a 22.6% conversion of methyl ester to benzyl ester.

Workup

  1. customwas collected
  2. customThe polymer was precipitated in methanol
  3. washthen washed with hexane
  4. dry with materialAfter drying at 55° C. overnight in an vacuum oven, 404 gram of polymer
  5. customwere recovered with a DSC melting point of 93-94° C

Sources & evidence

ORD record
ord-becace0325cb46048c17806bc2cd7f88
Source dataset
uspto-grants-2005_06
Patent number
US06906146B2

Reaction notes

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