Sodium Hydroxide → HCID 19080418, compound

Participants

Reaction Steps

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).

Provenance & Evidence