Acetic Acid → ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1457318노트

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HRID 1457318 반응식
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[H-].[Na+].[C:11]1(=[O:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1.C(O)(=O)C>C1(C)C=CC=CC=1>[O:21]=[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH:12]1[C:1]([O:5][CH2:6][CH3:7])=[O:8]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7766Diethyl CarbonateHCID 107241-TetraloneHCID 24758Sodium hydride

생성물 1

HCID 251472ethyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate수율 63%

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
50 °C

실험 절차

To a solution of diethyl carbonate (200 g) in toluene (800 ml) was added 60% sodium hydride (27.4 g), and the mixture was stirred at 50° C. for 30 minutes, and thereto was added dropwise a solution of 3,4-dihydro-1(2H)-napthalenone (50 g) in toluene (200 ml). The mixture was refluxed for one hour, and poured into ice-water, and the mixture was neutralized with acetic acid. The toluene layer was collected, washed successively with an aqueous potassium carbonate solution and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by distillation under reduced pressure to give ethyl 1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate (47 g) as an oily product, b.p. 135°-145° C./2 mmHg.

후처리

  1. temperatureThe mixture was refluxed for one hour
  2. customThe toluene layer was collected
  3. washwashed successively with an aqueous potassium carbonate solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. distillationThe residue was purified by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-ccd3562d52f5491f91209436dbc6d95f
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05847159

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