HCID 13723674, compound → HCID 13723663, compound

HRID 1448968Notes

Reaction equation

HRID 1448968 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]([C:17]1[CH:28]=[CH:27][C:20]2[O:21][CH:22]([CH2:25][OH:26])[CH2:23][O:24][C:19]=2[CH:18]=1)(=[O:16])[CH3:15]>CC(C)=O.C(O)(C)C.O.C(Cl)(Cl)Cl>[C:14]([C:17]1[CH:28]=[CH:27][C:20]2[O:21][CH:22]([C:25]([OH:3])=[O:26])[CH2:23][O:24][C:19]=2[CH:18]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 13723674HCID 13723674, compoundHCID 131709961Jones' reagent

Product 1

HCID 13723663HCID 13723663, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 18472940HCID 18472940, compoundSolvent

Procedure

Jones' reagent (11.6 ml.) was added dropwise to a stirred solution of 6-acetyl-2-hydroxymethyl-1,4-benzodioxan (4.0 g.) in acetone (70 ml.) at 10°-15° C. The reaction was stirred at room temperature for 18 hours then diluted with isopropanol/water/chloroform, the organic layer separated and evaporated in vacuo. The residue was redissolved in chloroform, extracted with saturated sodium carbonate solution (2×30 ml.) then the basic phase washed with chloroform, cooled and acidified to pH 1 with concentrated hydrochloric acid. The acidic solution was extracted with chloroform, the combined extracts washed with saturated brine, dried (Na2SO4) and evaporated in vacuo to give 6-acetyl-1,4-benzodioxan-2-carboxylic acid (1.56 g.), m.p. 159°-162° C. A sample was recrystallized from ethanol/ethyl acetate, m.p. 174°-175° C.

Workup

  1. customthe organic layer separated
  2. customevaporated in vacuo
  3. dissolutionThe residue was redissolved in chloroform
  4. extractionextracted with saturated sodium carbonate solution (2×30 ml.)
  5. washthe basic phase washed with chloroform
  6. temperaturecooled
  7. extractionThe acidic solution was extracted with chloroform
  8. washthe combined extracts washed with saturated brine
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-66e2113b7009424da3410aacad1f3200
Source dataset
uspto-grants-1980_02
Patent number
US04188390

Reaction notes

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