p-Anisoyl chloride → HCID 14257798, compound

HRID 2292061Notes

Reaction equation

HRID 2292061 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[OH:16][C:17]1[C:25]2[O:24][CH:23]=[C:22]([CH3:26])[C:21]=2[CH:20]=[C:19]([CH3:27])[C:18]=1[CH3:28]>ClCCCl>[OH:16][C:17]1[C:25]2[O:24][C:23]([C:1](=[O:10])[C:2]3[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=3)=[C:22]([CH3:26])[C:21]=2[CH:20]=[C:19]([CH3:27])[C:18]=1[CH3:28]

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14257796HCID 14257796, compound

Product 1

HCID 14257798HCID 14257798, compoundYield 189.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To p-anisoyl chloride (205 g) in 1,2-dichloroethane (2 L), cooled to 0° C., was added AlCl3 (240 g). The reaction mixture was warmed to room temperature and a solution of 7-hydroxy-3,5,6-trimethylbenzofuran (51 g) in 1,2-dichloroethane (400 mL) was added dropwise. The reaction was stirred for 51/2h then quenched with H2O (2 L). The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined extracts were washed with 25% NH4OAc buffer, dried (Na2SO4) and filtered on silica gel to give 170 g of crude material which was used as such in the next step.

Workup

  1. customthen quenched with H2O (2 L)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined extracts were washed with 25% NH4OAc buffer
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered on silica gel

Sources & evidence

ORD record
ord-528784d565b848b09a69cd82514844d2
Source dataset
uspto-grants-1989_01
Patent number
US04800228

Reaction notes

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