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

HRID 982088

Reaction equation

HRID 982088 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-1a0f3b468b924915a21701bcc37d5280
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Linked notes

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