Acetic Acid → Methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 478025ノート

反応式

HRID 478025 の反応式
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH2:17][C:18]2=[O:21])=[CH:13][CH:12]=1.C(O)(=O)C>CCCCCC.O1CCCC1.CCOCC.O>[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH:17]([C:3]([O:6][CH3:7])=[O:8])[C:18]2=[O:21])=[CH:13][CH:12]=1

参加物

9

反応物 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

生成物 1

HCID 14722817Methyl 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

A 50% slurry of NaH (30 g, 0.62 moles) in hexane was filtered through a fritted glass funnel to remove the mineral oil. The NaH was then added to a 2L flask, covered with 300 ml of tetrahydrofuran (THF), and placed under a N2 atmosphere. Upon the addition of 0.62 moles of dimethyl carbonate at one time with stirring, the reaction mixture was heated to 40°-50° C., whereupon 50 g (0.28 moles) of commerically available 7-methoxy-1-tetralone in 150 ml of THF was added at a rate to minimize foaming (1 hr.). Afte refluxing the reaction mixture for 2 hrs., the solution (red) was cooled to room temperature and slowly acidified by the addition of 45 ml of acetic acid. The resulting paste was dissolved upon addition of 50 ml of water. Ether was added and the layers were separated. The organic phase was washed with H2O, 3% NaHCO3 solution, and dried (Na2SO4 ). After filtration, the solvent was evaporated on a rotary evaporator. The residue was distilled at 168°-170° C. at 0.2 mm Hg.

後処理

  1. customto remove the mineral oil
  2. additionThe NaH was then added to a 2L flask
  3. additionwas added at a rate
  4. customfoaming (1 hr.)
  5. temperatureAfte refluxing the reaction mixture for 2 hrs
  6. customthe layers were separated
  7. washThe organic phase was washed with H2O, 3% NaHCO3 solution
  8. dry with materialdried (Na2SO4 )
  9. filtrationAfter filtration
  10. customthe solvent was evaporated on a rotary evaporator
  11. distillationThe residue was distilled at 168°-170° C. at 0.2 mm Hg

出典と根拠

ORDレコード
ord-a475edc7de30413886861d8b647eacf2
出典データセット
uspto-grants-1989_12
特許番号
US04889871

反応ノート

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