Water → HCID 19001695, compound

HRID 1195306Notes

Reaction equation

HRID 1195306 reaction equation
[C:1]([CH2:3][C:4]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)#N.[OH2:16].[OH-:17].[Na+]>C(O)C>[CH:13]([C:12]1[C:4]([CH2:3][C:1]([OH:17])=[O:16])=[CH:5][C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19001673HCID 19001673, compound

Product 1

HCID 19001695HCID 19001695, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.22 g of 5-cyanomethyl-6-isopropyl-1,3-benzodioxole (crude oil) was dissolved in 120 ml of ethanol, followed by the addition of 40 ml of water and 12.24 g of sodium hydroxide. The obtained mixture was stirred for 20 hours, while keeping the temperature of an oil bath at 100° C. The reaction mixture was concentrated, followed by the addition of water. The obtained mixture was washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to obtain 6.31 g of the title compound as a crude crystal.

Workup

  1. customat 100° C
  2. concentrationThe reaction mixture was concentrated
  3. additionfollowed by the addition of water
  4. washThe obtained mixture was washed with ethyl acetate
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5fa5a0a5068741f0ac410deac0f3f6ae
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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