Water → 2-(4-Fluorobenzyl)malonic acid

HRID 1507299Notes

Reaction equation

HRID 1507299 reaction equation
[F: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+].O>C(OCC)(=O)C>[F: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

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 860963525-(4-Fluorobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 151206432-(4-Fluorobenzyl)malonic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(4-fluorobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (34.118 g, 135.26 mmol, Intermediate 7: step a) and 6 M aqueous NaOH (136 mL) was heated to 120° C. under a reflux condenser and positive pressure of nitrogen for two days. The mixture was allowed to cool to room temperature, water and ethyl acetate were added, and the layers were separated. The aqueous layer was acidified to pH 0 with 6 M aqueous HCl and the mixture was stirred at room temperature for 30 minutes. Dichloromethane was added to the mixture, the organic layer was separated, and the aqueous layer was extracted with excess ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness to provide the title compound.

Workup

  1. customthe layers were separated
  2. additionDichloromethane was added to the mixture
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with excess ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ef908c528695471480092afbf7862068
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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