Aluminum(III) Chloride → HCID 13714036, compound
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH:9]=[C:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1C(Cl)=CC=C(Cl)C=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:8](=[O:13])[CH2:9][C:10]2([CH3:11])[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a stirred solution of 1-(4-hydroxyphenyl)-3-methylbut-2-en-1-one (1.0 g, 5.67 mmol) in dichlorobenzene (50 mL) was added aluminum chloride (1.97 g, 14.74 mmol). The mixture was heated to 150° C. for 4 hours. After cooled to room temperature, the reaction mixture was poured over ice and extracted with dichloromethane (3×80 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a silica gel column (20% ethyl acetate in hexane) to give 5-hydroxy-3,3-dimethylindan-1-one as a tan solid (0.32 g, 32%). MS m/z 177.
Workup
- temperatureAfter cooled to room temperature
- additionthe reaction mixture was poured over ice
- extractionextracted with dichloromethane (3×80 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified on a silica gel column (20% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-5a24806cd6454345a2303e57650a6fb5
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414142B2
Reaction notes
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