Aluminum(III) Chloride → 6-Methoxy-2-phenylindan-1-one

HRID 1935736Notes

Reaction equation

HRID 1935736 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](Cl)=[O:16])=[CH:9][CH:8]=1>ClCCl>[CH3:5][O:6][C:7]1[CH:12]=[C:11]2[C:10]([CH2:13][CH:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]2=[O:16])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 111403233-(4-Methoxyphenyl)-2-phenylpropionyl chloride

Product 1

HCID 224653766-Methoxy-2-phenylindan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum chloride (345 mg) and one quarter of the crude 3-(4-methoxyphenyl)-2-phenylpropionyl chloride from the previous step were added to dry dichloromethane (45 ml) at 0° C. After 1 hour aluminum chloride (345 mg) and the second quarter of the acid chloride were added. Stirring was continued and the addition was repeated twice again. After the last addition stirring was continued for half an hour at 0° C. and then 2 hours at room temperature. The reaction mixture was poured into ice-cold diluted acidic water. The organic phase was separated and the water phase was extracted twice with dichloromethane. The combined organic phases were washed with water, 2.5% sodium hydroxide solution in water and again with water. The dichloromethane solution was dried and evaporated.

Workup

  1. additionthe addition
  2. additionAfter the last addition
  3. stirringstirring
  4. waitwas continued for half an hour at 0° C.
  5. custom2 hours
  6. customat room temperature
  7. additionThe reaction mixture was poured into ice-cold diluted acidic water
  8. customThe organic phase was separated
  9. extractionthe water phase was extracted twice with dichloromethane
  10. washThe combined organic phases were washed with water, 2.5% sodium hydroxide solution in water and again with water
  11. dry with materialThe dichloromethane solution was dried
  12. customevaporated

Sources & evidence

ORD record
ord-9af6f09c08284dd9b59a4f648b79363f
Source dataset
uspto-grants-2002_05
Patent number
US06388090B2

Reaction notes

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