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

HRID 982088

반응식

HRID 982088 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 122124065-Methoxy-3-phenyl-1-tetralone수율 36.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매

반응 조건

온도
60 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-1a0f3b468b924915a21701bcc37d5280
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994486

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