Water → 68281-27-6

HRID 1448970Notes

Reaction equation

HRID 1448970 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH2:15][C:16]1([CH3:26])[O:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1.C(O)(C)C.O>CC(C)=O>[CH3:26][C:16]1([C:15]([OH:3])=[O:14])[O:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 3778286HCID 3778286, compoundHCID 131709961Jones' reagent

Product 1

HCID 1263753668281-27-6

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (33.3 ml.) was added dropwise to a stirred solution of 2-hydroxymethyl-2-methyl-1,4-benzodioxan (5 g.) in acetone (300 ml.) at 5° C., then the reaction was allowed to attain room temperature. Isopropanol (10 ml.) was then added followed by water (200 ml.), the solution extracted with chloroform and the extracts evaporated in vacuo. The residual oil was taken up in chloroform (200 ml.) then extracted with dilute sodium bicarbonate solution and the aqueous phase further washed with chloroform. The aqueous phase was then acidified with hydrochloric acid, extracted with chloroform, the combined extracts washed with water, dried (MgSO4) and evaporated in vacuo ti give 2-methyl-1,4-benzodioxan-2-carboxylic acid (1.7 g.). A sample was recrystallized from toluene, m.p. 133°-134° C.

Workup

  1. customto attain room temperature
  2. extractionthe solution extracted with chloroform
  3. customthe extracts evaporated in vacuo
  4. extractionthen extracted with dilute sodium bicarbonate solution
  5. washthe aqueous phase further washed with chloroform
  6. extractionextracted with chloroform
  7. washthe combined extracts washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo ti

Sources & evidence

ORD record
ord-d563cede87794726a093147db6fd5851
Source dataset
uspto-grants-1980_02
Patent number
US04188390

Reaction notes

Loading…