Toluene → 2-Propenoic acid, 2-methyl-, 2-(2-propen-1-yloxy)ethyl ester

HRID 1603175

반응식

HRID 1603175 반응식
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([O:10][CH2:11][CH2:12]O)[CH:8]=[CH2:9].C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:1]([O:6][CH2:12][CH2:11][O:10][CH2:7][CH:8]=[CH2:9])(=[O:5])[C:2]([CH3:4])=[CH2:3]

참가 물질

6

반응물 3

HCID 1140TolueneHCID 4093Methacrylic AcidHCID 8116Ethylene glycol monoallyl ether

생성물 1

HCID 856092-Propenoic acid, 2-methyl-, 2-(2-propen-1-yloxy)ethyl ester수율 73%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매3회HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

To a three-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a Dean-Stark apparatus were added methacrylic acid (137.7 g, 1.6 moles), ethyleneglycol monoallylether (80.7 g, 0.8 moles), p-toluenesulfonic acid (0.76 g, 4.0 mmole) and toluene (650 mL). The mixture was heated to 120° C. for 5 hours with exclusion of water. Another portion of p-toluenesulfonic acid (0.12 g) and the mixture was heated to 120° C. for 6 hours. The other portion of p-toluenesulfonic acid (0.1 g) was added and the mixture was heated to 120° C. for 9 hours. During the reaction, the consumption of methacrylic acid and ethyleneglycol monoallylether were monitored by liquid chromatography and the conversion reached 98%. The mixture was neutralized by addition of aq. NaHCO3 and the layers were separated. The aqueous layer was extracted with toluene and the combined organic layers were dried over CaCl2 and concentrated under reduced pressure. Distillation of the crude material (60° C. at 2 mmHg) yielded 2-allyloxyethyl methacrylate (98.7 g, 73%) shown below.

후처리

  1. customTo a three-necked flask equipped with a stirrer
  2. customDuring the reaction
  3. customthe consumption of methacrylic acid and ethyleneglycol monoallylether
  4. additionThe mixture was neutralized by addition of aq. NaHCO3
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with toluene
  7. dry with materialthe combined organic layers were dried over CaCl2
  8. concentrationconcentrated under reduced pressure
  9. distillationDistillation of the crude material (60° C. at 2 mmHg)

출처 및 근거

ORD 기록
ord-c8f8bbbccf144cedbb0ffef76f2f44b6
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986014

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