Hydrochloric Acid → 2,2-dimethylbenzo[d][1,3]dioxol-5-ol

HRID 731977Notes

Reaction equation

HRID 731977 reaction equation
C([O:4][C:5]1[CH:15]=[CH:14][C:8]2[O:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)(=O)C.[OH-].[K+].Cl>CO.O>[CH3:12][C:10]1([CH3:13])[O:9][C:8]2[CH:14]=[CH:15][C:5]([OH:4])=[CH:6][C:7]=2[O:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13047627HCID 13047627, compound

Product 1

HCID 142047412,2-dimethylbenzo[d][1,3]dioxol-5-olYield 72.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 0.6 gram (0.003 mole) of 2,2-dimethylbenzo[3,4-d]1,3-dioxolan-5-yl acetate in 5 mL of methanol was stirred and a solution of 1.1 grams (0.02 mole) of potassium hydroxide in 5 mL of water was added in one portion. Upon completion of addition the reaction mixture was stirred at ambient temperature during a two hour period. After this time the reaction mixture was diluted with 50 mL of water and acidified with concentrated hydrochloric acid. The mixture was then extracted with two 100 mL portions of ethyl acetate. The combined extracts were dried with sodium sulfate, filtered and concentrated under reduced pressure, yielding 0.36 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. extractionThe mixture was then extracted with two 100 mL portions of ethyl acetate
  3. dry with materialThe combined extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8783edaca2424e159ee34ba866142e94
Source dataset
uspto-grants-2009_09
Patent number
US07585891B2

Reaction notes

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