Aluminum(III) Chloride → 5-Methoxy-3-phenyl-1-tetralone

HRID 982088

反応式

HRID 982088 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][C:12]([OH:14])=O.[Cl-].[Al+3].[Cl-].[Cl-]>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[CH2:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][C:12]2=[O:14]

参加物

5

反応物 2

HCID 6451240Aluminum(III) ChlorideHCID 122124054-(2'-Methoxyphenyl)-3-phenylbutyric acid

生成物 1

HCID 122124065-Methoxy-3-phenyl-1-tetralone収率 36.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒

反応条件

温度
60 °C

実験手順

4-(2'-Methoxyphenyl)-3-phenylbutyric acid (29.1 g, 108 mmol), from Step 5, was dissolved in 50 mL of thionyl chloride and heated to 60° C. for 10 min. After stirring an additional 30 min at ambient temperature, the solvent was removed in vacuo. The crude product was dissolved in 60 mL of methylene chloride and the resultant solution was added dropwise to 15.8 g (118 mmol) of aluminum chloride in 240 mL of methylene chloride precooled to 0° C. After the addition, the reaction was allowed to proceed at 0° C. for 1 h, and then quenched by the addition of 500 g of ice. The methylene chloride layer was separated and washed with 3×200 mL of water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 9.84 g (36% yield) of 5-methoxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalenone as a clear yellow oil; 1H NMR (CDCl3 )δ2.48 (dd, 1H), 2.65-2.8 (m, 2H), 3.20 (dd, 1H), 3.7-3.85 (m, 1H), 3.82 (s, 3H), 6.85-6.95 (m, 2H), 7.08 (dd, 1H), 7.2-7.3 (m, 1H), 7.35-7.4 (m, 2H), 7.57 (dt, 1H), 7.73 (d, 1H); DCl MS M/Z: 270 (M+NH4)+, 253 (M+H)+.

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionThe crude product was dissolved in 60 mL of methylene chloride
  3. customprecooled to 0° C
  4. additionAfter the addition
  5. waitto proceed at 0° C. for 1 h
  6. customquenched by the addition of 500 g of ice
  7. customThe methylene chloride layer was separated
  8. washwashed with 3×200 mL of water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1a0f3b468b924915a21701bcc37d5280
出典データセット
uspto-grants-1991_02
特許番号
US04994486

関連ノート

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