4-Chlorophenol → HCID 18348662, compound

HRID 2268498Notes

Reaction equation

HRID 2268498 reaction equation
I[CH2:2][CH2:3][CH:4]1[CH2:10][CH2:9][C:8]2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:7]=2[CH2:6][CH2:5]1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:2][CH2:3][CH:4]2[CH2:10][CH2:9][C:8]3[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:7]=3[CH2:6][CH2:5]2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 183485187-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene

Product 1

HCID 18348662HCID 18348662, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 7-(2-iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene (1.64 g), 4-chlorophenol (602 mg), potassium carbonate (1.08 g), and DMF (16 ml) was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by alumina column chromatography (toluene) to yield the entitled compound (1.58 g) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by alumina column chromatography (toluene)

Sources & evidence

ORD record
ord-fac5cf870fdd416eb5f243a2f3c0ba3d
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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