Chromic Acid → HCID 13645870, compound

HRID 1982267Notes

Reaction equation

HRID 1982267 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[O:11][C:10]2[C:12]([Cl:19])=[C:13]([Cl:18])[CH:14]=[C:15]([CH:16]=[O:17])[C:9]=2[O:8][CH2:7]1)(=[O:3])[CH3:2].[Cr](O)(O)(=O)=[O:21]>CC(C)=O>[C:1]([O:4][CH2:5][CH:6]1[O:11][C:10]2[C:12]([Cl:19])=[C:13]([Cl:18])[CH:14]=[C:15]([C:16]([OH:21])=[O:17])[C:9]=2[O:8][CH2:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24425Chromic AcidHCID 13645808HCID 13645808, compound

Product 1

HCID 13645870HCID 13645870, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.03 g of 2-acetoxymethyl-7,8-dichloro-1,4-benzodioxane-5-carbaldehyde (Ia-a-39) in 70 ml of acetone is added 2 ml of 8N-chromic acid/sulfric acid. The mixture is stirred at room temperature for about 2.5 hours and then filtered after the confirmation by TLC that no starting material is remained. The filtrate is concentrated under reduced pressure to give a residue, which is extracted with dichloromethane. The organic layer is washed with water and evaporated to give 1.004 g (93%) of 2-acetoxymethyl-7,8-dichloro-1,4-benzodioxane-5-carboxylic acid (Ia-a-43: R3 '=Ac), which is recrystallized from dichloromethane/ether to yield crystals, m.p. 144°-145° C.

Workup

  1. filtrationfiltered after the confirmation by TLC that no starting material
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customto give a residue, which
  4. extractionis extracted with dichloromethane
  5. washThe organic layer is washed with water
  6. customevaporated

Sources & evidence

ORD record
ord-90cae9718e6c4d91808bfef5a7b494d4
Source dataset
uspto-grants-1986_06
Patent number
US04595767

Reaction notes

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