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

HRID 526837Notes

Reaction equation

HRID 526837 reaction equation
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][CH:10]2[C:15](=[O:16])[O:14]C(C)(C)[O:12][C:11]2=[O:19])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+]>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]([C:11]([OH:19])=[O:12])[C:15]([OH:16])=[O:14])=[CH:20][CH:21]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 867155855-(4-Methylsulfonylbenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 867155862-(4-Methylsulfonylbenzyl)malonic acid

Procedure

A solution of 5-(4-methylsulfonylbenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.50 g, 4.80 mmol, Intermediate 6: 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×). The aqueous layer was acidified to pH 1 with concentrated aqueous HCl and extracted with EtOAc (2 x). The combined EtOAc extracts was washed with H2O, brine, dried over Na2SO4, filtered and evaporated to dryness to afford the title compound as a white solid.

Workup

  1. extractionThe aqueous mixture was extracted with EtOAc (1×)
  2. extractionextracted with EtOAc (2 x)
  3. washThe combined EtOAc extracts was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f63fe2d1d9c44b87b4c16ea7630ec059
Source dataset
uspto-grants-2016_05
Patent number
US09346782B2

Reaction notes

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