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

HRID 1457318ノート

反応式

HRID 1457318 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ccd3562d52f5491f91209436dbc6d95f
出典データセット
uspto-grants-1998_12
特許番号
US05847159

反応ノート

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