Anisole → HCID 14570900, compound

HRID 1534254Notes

Reaction equation

HRID 1534254 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:20])=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[C:5]([Cl:21])=[CH:4][C:3]=1C(C)(C)C.C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[OH:1][C:2]1[C:7]2[C:8]([CH3:20])=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[C:5]([Cl:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 14570891HCID 14570891, compound

Product 1

HCID 14570900HCID 14570900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution (0° C) of 4-hydroxy-7-chloro-5-t-butyl-2-(4'-methoxyphenylmethyl)-3-methylbenzofuran(165) (Example 43) (10 g, 27.8 mmol) in 500 mL dichloromethane was added 5 mL of anisole followed by aluminum chloride (13 g, 0.1 mol) in portions. The mixture was allowed to stir for 1 h and then poured onto ice. The mixture was extracted with dichloromethane, the organic extracts were dried, concentrated and chromatographed to give the title compound.

Workup

  1. additionpoured onto ice
  2. extractionThe mixture was extracted with dichloromethane
  3. customthe organic extracts were dried
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-c97e2b7bf79643e58d5b9b78e58d37ba
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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