Methyl Methacrylate → 4-Phenylbutyl methacrylate

HRID 1860227

Reaktionsgleichung

Reaktionsgleichung von HRID 1860227
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:8](OCCCO)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:20](OC1C=CC(O)=CC=1)[C:21]1C=CC=CC=1>[O-]CCCC.[O-]CCCC.[O-]CCCC.[O-]CCCC.[Ti+4]>[C:1]([O:6][CH2:7][CH2:20][CH2:21][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Komponenten

5

Edukt 3

HCID 6658Methyl Methacrylate2×HCID 7638MonobenzoneHCID 3479713-Benzyloxy-1-propanol

Produkt 1

HCID 225074774-Phenylbutyl methacrylateAusbeute 213,7 %

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 95 mL (0.884 mol) of methyl methacrylate (2), 4.22 g (0.012 mol) of titanium tetrabutoxide (Ti(OC4H9)4), 50 mL (0.316 mol) of 3-benzyloxy-1-propanol (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 36.5 g (0.156 mol, 49%) of 3-benzyloxypropyl methacrylate (3) as a clear, colorless liquid.

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-ef8fb2826a9c41fb81d8c64e3f1f9f63
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528602B1

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