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

HRID 1507308Notes

Reaction equation

HRID 1507308 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, 4.802 mmol, Intermediate 12: 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×). The combined EtOAc extracts were washed with H2O, and 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×)
  3. washThe combined EtOAc extracts were washed with H2O, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b8cfff632c2640e18e376cca77c65d28
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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