Sodium Hydroxide → HCID 19080418, compound

HRID 865520Notes

Reaction equation

HRID 865520 reaction equation
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([O:9][C:10]2[C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=[CH:12][C:11]=2[CH2:19][C:20]([O:22]CC)=[O:21])=[C:7]([CH2:27][CH2:28][CH3:29])[CH:6]=1)([O:3][CH3:4])=[O:2].[OH-].[Na+]>CO>[C:1]([C:5]1[CH:26]=[CH:25][C:8]([O:9][C:10]2[C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=[CH:12][C:11]=2[CH2:19][C:20]([OH:22])=[O:21])=[C:7]([CH2:27][CH2:28][CH3:29])[CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19080411HCID 19080411, compound

Product 1

HCID 19080418HCID 19080418, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl 2-(4-carbomethoxy-2-propylphenoxy)-3,4-methylenedioxyphenylacetate (Step A of Example 56) (2.04 g, 5.10 mmol) in MeOH (40 mL) was added 5 N NaOH (8 mL). The rapid reaction was followed immediately by TLC to monitor mono deesterification. The reaction was quenched with 9 N HCl (4.5 mL) after loss of the ethyl ester and before methyl ester saponification. A saturated solution of NaHCO3 was added to the reaction until it was basic and the MeOH was removed in vacuo. The residue was partitioned between Et2O and water collecting the product in the aqueous phase and removing impurities with the organic phase. The aqueous phase was then acidified with 9 N HCl (pH=1) and the product extracted into EtOAc. The solution was dried over MgSO4, filtered and the solvent removed. yield=1.78 g (4.78 mmol, 94%) rf=0.16 (80:10:1/CHCl3 :MeOH:NH4OH).

Workup

  1. customThe rapid reaction
  2. customThe reaction was quenched with 9 N HCl (4.5 mL) after loss of the ethyl ester
  3. additionA saturated solution of NaHCO3 was added to the reaction until it
  4. customthe MeOH was removed in vacuo
  5. customThe residue was partitioned between Et2O and water collecting the product in the aqueous phase
  6. customremoving impurities with the organic phase
  7. extractionthe product extracted into EtOAc
  8. dry with materialThe solution was dried over MgSO4
  9. filtrationfiltered
  10. customthe solvent removed

Sources & evidence

ORD record
ord-dff6ed1fa03d435b904326e66251f128
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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