Acetyl chloride → 1-[3-(Methoxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethan-1-one

HRID 2308188Notes

Reaction equation

HRID 2308188 reaction equation
[CH3:1][C:2](N(C)C)=[O:3].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][O:12][CH2:13][CH:14]1[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15]1.C(Cl)(=O)C>>[CH3:11][O:12][CH2:13][CH:14]1[CH2:15][O:16][C:17]2[CH:23]=[CH:22][C:21]([C:2]([CH3:1])=[O:3])=[CH:20][C:18]=2[O:19]1

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 31374DimethylacetamideHCID 6451240Aluminum(III) ChlorideHCID 121346011,4-Benzodioxin, 2,3-dihydro-2-(methoxymethyl)-

Product 1

HCID 154214401-[3-(Methoxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethan-1-one

Procedure

Dimethyl acetamide (16.65 mol, 1.31 ml) was added slowly to anhydrous aluminum chloride (33.3 mmol, 4.44 g) at 0° C. in the presence of nitrogen and stirred for 30 min at a room temperature, and then, the titled compound prepared in Example 1 (3.77 mmol, 500 mg) was added slowly to the resulting mixture, followed by stirring for 15 min. Then, acetyl chloride (3.33 mmol, 0.28 ml) was added and stirred for 5 hours at a room temperature. Ice was added slowly to the mixture to destroy and remove the remaining aluminum chloride. The reaction mixture was neutralized with NaHCO3, extracted with ethylacetate, followed by removing the solvent. And then, the resultant was dried to prepare the titled compound (520 mg, 84%).

Workup

  1. stirringby stirring for 15 min
  2. stirringstirred for 5 hours at a room temperature
  3. additionIce was added slowly to the mixture
  4. customto destroy
  5. customremove the remaining aluminum chloride
  6. extractionextracted with ethylacetate
  7. customby removing the solvent
  8. customAnd then, the resultant was dried
  9. customto prepare the titled compound (520 mg, 84%)

Sources & evidence

ORD record
ord-f410b7982533434db2fc18e3dfbdc738
Source dataset
uspto-grants-2004_12
Patent number
US06835735B2

Reaction notes

Loading…