Sodium Hydroxide → HCID 18992020, compound

HRID 375751Notes

Reaction equation

HRID 375751 reaction equation
CN[C:3]([C:5]1[CH:25]=[CH:24][C:8]2[O:9][C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[C:6]=1[CH3:26])=[O:4].[OH-:27].[Na+]>C(O)CO>[CH3:26][C:6]1[C:7]2[O:11][C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9][C:8]=2[CH:24]=[CH:25][C:5]=1[C:3]([OH:27])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18991991HCID 18991991, compound

Product 1

HCID 18992020HCID 18992020, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 1.60 g of N,4-dimethyl-2,2-diphenyl-1,3-benzodioxole-5-carboxamide and 1.00 g of sodium hydroxide in 10 ml of ethylene glycol was heated to 190° C. for 2.5 hours. After cooling, the mixture was partitioned between water and ethyl acetate. The aqueous phase was washed with ethyl acetate, adjusted to pH 2 by the addition of 3N hydrochloric acid, and then the product was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the solid residue was crystallized from ethanol to give 0.53 g of 4-methyl-2,2-diphenyl-1,3-benzodioxole-5-carboxylic acid, m.p. 263°-265° C.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between water and ethyl acetate
  3. washThe aqueous phase was washed with ethyl acetate
  4. additionadjusted to pH 2 by the addition of 3N hydrochloric acid
  5. extractionthe product was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customthe solid residue was crystallized from ethanol

Sources & evidence

ORD record
ord-7e9439e9c42b4472bb0ca6be3971df5a
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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