2,2-Dimethyl-5-(3-(trifluoromethyl)benzyl)-1,3-dioxane-4,6-dione → 2-(3-(Trifluoromethyl)benzyl)malonic acid

HRID 1507314Notes

Reaction equation

HRID 1507314 reaction equation
CC1(C)[O:7][C:6](=[O:8])[CH:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:4](=[O:20])[O:3]1>[OH-].[Na+]>[F:17][C:16]([F:18])([F:19])[C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][CH:5]([C:6]([OH:8])=[O:7])[C:4]([OH:20])=[O:3]

Participants

3

Reactant 1

HCID 1180062772,2-Dimethyl-5-(3-(trifluoromethyl)benzyl)-1,3-dioxane-4,6-dione

Product 1

HCID 665199072-(3-(Trifluoromethyl)benzyl)malonic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2,2-dimethyl-5-(3-(trifluoromethyl)benzyl)-1,3-dioxane-4,6-dione (4.0 g, 13.23 mmol, Intermediate 15: step a) in 40% aqueous NaOH (20 mL) was heated in a 93° C. oil bath for 48 hours. The mixture was then cooled to room temperature and extracted with EtOAc. The aqueous layer was acidified to pH 2 with 6 N aqueous HCl then extracted with EtOAc (2×). The combined EtOAc extracts were washed with H2O followed by brine and dried over Na2SO4. The mixture was filtered, solvent was removed under reduced pressure and crude product purified by chromatography (10% MeOH/0.2% HOAc mixture in DCM) to afford the title compound as an off-white solid.

Workup

  1. extractionextracted with EtOAc
  2. extractionthen extracted with EtOAc (2×)
  3. washThe combined EtOAc extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationThe mixture was filtered
  6. customsolvent was removed under reduced pressure and crude product
  7. custompurified by chromatography (10% MeOH/0.2% HOAc mixture in DCM)

Sources & evidence

ORD record
ord-9b08eb97823a4b589e69576821e10ee5
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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