Sodium Hydroxide → HCID 9820155, compound

HRID 743989Notes

Reaction equation

HRID 743989 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CCO>[C:23]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:9]([OH:11])=[O:10])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15839227HCID 15839227, compound

Product 1

HCID 9820155HCID 9820155, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Methyl 3,3-diphenyl-2-(3,4-methylenedioxybenzyl)prop-2-enoate (0.05 g, 0.13 mmol) was dissolved in EtOH (2 ml) and 3M aqueous NaOH added (2 mi, 6 mmol). After stirring at 80° C. for 15 h the EtOH was removed in vacuo and the residue partitioned between EtOAc and H2O. The aqueous layer was acidified to pH 2 with 1-M-aqueous HCl and extracted with EtOAc (3X). The combined organic extract was washed with brine, dried (MgSO4 anhydrous), filtered and evaporated to give a colorless solid. Recrystallization from EtOAc/hexane gave the title compound as a colorless solid (0.037 g, 77%).

Workup

  1. customwas removed in vacuo
  2. customthe residue partitioned between EtOAc and H2O
  3. extractionextracted with EtOAc (3X)
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4 anhydrous)
  7. filtrationfiltered
  8. customevaporated
  9. customto give a colorless solid
  10. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-cb1a3aa09715414099c467bc458f3d7d
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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