Sodium Hydroxide → 2-(4-Chlorobenzyl)malonic acid

HRID 928713Notes

Reaction equation

HRID 928713 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[C:12](=[O:13])[O:11]C(C)(C)[O:9][C:8]2=[O:16])=[CH:4][CH:3]=1.[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([C:8]([OH:16])=[O:9])[C:12]([OH:13])=[O:11])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 108801105-(4-Chlorobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 27851452-(4-Chlorobenzyl)malonic acid

Procedure

A solution of 5-(4-chlorobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.50 g, 5.58 mmol, Intermediate 3: step a) and 3 M aqueous NaOH (16 mL) was heated in the microwave at 75 W for 20 minutes at 120° C. The aqueous mixture was extracted with EtOAc (1×) then acidified to pH 1 with concentrated aqueous HCl and extracted with EtOAc (2×). The combined EtOAc extract was washed with H2O, brine and dried over Na2SO4, filtered. Solvents were removed under reduced pressure to afford the title compound as a white solid.

Workup

  1. extractionThe aqueous mixture was extracted with EtOAc (1×)
  2. extractionextracted with EtOAc (2×)
  3. extractionThe combined EtOAc extract
  4. washwas washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-9179cf23b1be415c92528971720d6131
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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