Aluminum(III) Chloride → 1,4-Benzodioxin-6-carboxaldehyde, 2,3-dihydro-7-hydroxy-

HRID 428151Notes

Reaction equation

HRID 428151 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C[O:6][C:7]1[C:8]([CH:17]=[O:18])=[CH:9][C:10]2[O:15][CH2:14][CH2:13][O:12][C:11]=2[CH:16]=1>C(Cl)Cl>[OH:6][C:7]1[C:8]([CH:17]=[O:18])=[CH:9][C:10]2[O:15][CH2:14][CH2:13][O:12][C:11]=2[CH:16]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 64970647-Methoxy-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

Product 1

HCID 141428211,4-Benzodioxin-6-carboxaldehyde, 2,3-dihydro-7-hydroxy-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4 eq. of AlCl3 are suspended in 10 ml of anhydrous CH2Cl2. Under an inert atmosphere, 100 mg (5.55 mmol) of the compound obtained in Step C, dissolved in 10 ml of anhydrous CH2Cl2, are added to that mixture and allowed to act for 2 hours at ambient temperature. The mixture is hydrolysed with an ice-cold 2N HCl solution; the solution is then extracted with CH2Cl2 and dried over MgSO4. After evaporation of the solvent, purification on a silica column (eluant:PE/AcOEt 7/3) is carried out and the pure product is isolated.

Workup

  1. additionare added to that mixture
  2. extractionthe solution is then extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of the solvent, purification on a silica column (eluant:PE/AcOEt 7/3)
  5. customthe pure product is isolated

Sources & evidence

ORD record
ord-90ea76596ca94c1eaf9b5c6cb614de49
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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