Methyl Methacrylate → 4-Phenylbutyl methacrylate

HRID 480989

Reaktionsgleichung

Reaktionsgleichung von HRID 480989
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8]1([CH2:14][CH2:15][CH2:16]CO)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OC1C=CC(O)=CC=1)C1C=CC=CC=1>[O-]CCCC.[O-]CCCC.[O-]CCCC.[O-]CCCC.[Ti+4]>[C:1]([O:6][CH2:7][CH2:16][CH2:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Komponenten

5

Edukt 3

HCID 6658Methyl Methacrylate2×HCID 7638MonobenzoneHCID 76889Benzenebutanol

Produkt 1

HCID 225074774-Phenylbutyl methacrylateAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21801Titanium tetrabutoxideKatalysator

Versuchsvorschrift

A three neck round bottom flask containing a teflon coated magnetic stirring bar was successively charged with 120 mL (1.09 mol) of methyl methacrylate (2), 5.35 g (0.015 mol) of titanium tetrabutoxide (Ti(OC4H9)4), 60 mL (0.39 mol) of 4-phenyl-1-butanol (1), and 14.6 g (0.073 mol) of 4-benzyloxyphenol (4-BOP). An addition funnel, thermometer, and a short path still head with thermometer and receiver flask were placed in the flask necks. The flask was placed in an oil bath and the temperature was increased until distillation began. Methyl methacrylate (2) was placed in the addition funnel and was added dropwise at the same rate as the distillate. The reaction mixture was heated for 4 hours and then cooled to room temperature. The crude product was vacuum distilled to isolate 62.8 g (0.29 mol, 74%) of 4-phenylbutyl methacrylate (3) as a clear, colorless liquid. Example 2: Synthesis of 3-benzyloxypropyl methacrylate.

Aufarbeitung

  1. additionA three neck round bottom flask containing a teflon coated magnetic stirring bar
  2. customAn addition funnel, thermometer, and a short path still head with thermometer and receiver flask were placed in the flask necks
  3. customThe flask was placed in an oil bath
  4. temperaturethe temperature was increased until distillation
  5. additionwas added dropwise at the same rate as the distillate
  6. temperatureThe reaction mixture was heated for 4 hours
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-09bad5a9cd8c487ba14ee78c83cf96c4
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653422B2

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