Malonic Acid → HCID 90410949, 화합물

HRID 717386노트

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HRID 717386 반응식
[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)[CH2:19][C:20]([OH:22])=[O:21].N1CCCCC1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:10]=1/[CH:11]=[CH:19]\[C:20]([OH:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 110641372-benzyloxy-3-methylbenzaldehyde

생성물 1

HCID 90410949HCID 90410949, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-(benzyloxy)-3-methylbenzaldehyde (20 g, 88.39 mmol, 1.00 equiv), propanedioic acid (27.6 g, 265.23 mmol, 3.00 equiv), piperidine (1.5 g, 17.62 mmol, 0.20 equiv) and pyridine (200 mL). The resulting solution was heated to reflux for 2 h in an oil bath. The reaction was then quenched by the addition of 1.5 L of water/ice. The pH value of the solution was adjusted to 2-3 with hydrogen chloride. The solids were collected by filtration. The filter cake was washed with 2×500 mL of water and 2×500 mL of hexane. This resulted in 21 g (89%) of (2Z)-3-[2-(benzyloxy)-3-methylphenyl]prop-2-enoic acid as a white solid. MS (ESI) m/z 269 ([M+H]+).

후처리

  1. customInto a 500-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 2 h in an oil bath
  5. customThe reaction was then quenched by the addition of 1.5 L of water/ice
  6. filtrationThe solids were collected by filtration
  7. washThe filter cake was washed with 2×500 mL of water and 2×500 mL of hexane
  8. customThis resulted in 21 g (89%) of (2Z)-3-[2-(benzyloxy)-3-methylphenyl]prop-2-enoic acid as a white solid

출처 및 근거

ORD 기록
ord-4cee676bfa1e4d41a8f64215f318eb57
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193707B2

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