2,3-Dichloroanisole → HCID 14012552, compound

HRID 652850Notes

Reaction equation

HRID 652850 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6](Cl)=[O:7])=[CH:2]1.[Cl:9][C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[O:17][CH3:18].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[O:1]1[CH:5]=[CH:4][C:3]([C:6]([C:14]2[CH:13]=[CH:12][C:11]([O:17][CH3:18])=[C:10]([Cl:9])[C:15]=2[Cl:16])=[O:7])=[CH:2]1

Participants

5

Reactant 3

HCID 161262,3-DichloroanisoleHCID 27761233-Furoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14012552HCID 14012552, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

3-Furoyl chloride (18.0 g) and 2,3-dichloro anisole (24.7 g) are dissolved in 125 ml of CS2 and treated with AlCl3 (18.7 g), first at 5° C. and then at room temperature. After five hours the reaction is quenched with ice/HCl and extracted with CH2Cl2. Drying and evaporation gives a crystalline product that is triturated with hexane to yield 4-(3-furoyl)-2,3-dichloroanisole, mp 118°-122° C.

Workup

  1. customat room temperature
  2. customAfter five hours the reaction is quenched with ice/HCl
  3. extractionextracted with CH2Cl2
  4. customDrying
  5. customevaporation
  6. customgives a crystalline product that
  7. customis triturated with hexane

Sources & evidence

ORD record
ord-ee81a7d8ee724418a3d9a2973788079e
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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