Aluminum(III) Chloride → 2-Methoxy-6-(3,4,5-trimethoxy-phenyl)-8,9-dihydro-7H-benzocyclohepten-1-ol

HRID 33952Notes

Reaction equation

HRID 33952 reaction equation
C([O:4][C:5]1[C:15]2[CH2:14][CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[CH:10][C:9]=2[CH:8]=[CH:7][C:6]=1[O:28][CH3:29])(C)C.[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH3:29][O:28][C:6]1[C:5]([OH:4])=[C:15]2[CH2:14][CH2:13][CH2:12][C:11]([C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)=[CH:10][C:9]2=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 689232404-Isopropoxy-3-methoxy-8-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-benzocycloheptene

Product 1

HCID 159861652-Methoxy-6-(3,4,5-trimethoxy-phenyl)-8,9-dihydro-7H-benzocyclohepten-1-olYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

41 (220 mg, 0.55 mmol) was dissolved in 15 mL of anhydrous dichlromethane under nitrogen at room temperature. Aluminium chloride (147 mg, 1.1 mmol) was added and the reaction mixture was stirred for 10 minutes. 10 mL of water was added and the product was extracted in dichloromethane (2×20 mL) and the combined organic phases were dried over anhydrous sodium sulfate, evaporated under reduced pressure purified by column chromatography. The product 3, 81 mg (41% yield) was obtained in 10% ethylacetate in hexanes. Rf. 0.54 (60:40 Hex:EA).

Workup

  1. extractionthe product was extracted in dichloromethane (2×20 mL)
  2. dry with materialthe combined organic phases were dried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-cc368efef19b482ca8cece0afca9d512
Source dataset
uspto-grants-2008_09
Patent number
US07429681B2

Reaction notes

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