1,4-Dioxane-2,6-dione → Diglycolic Acid

HRID 2417149Notes

Reaction equation

HRID 2417149 reaction equation
C[O:2]C1C=CC(C(OCC(CO)(C(OCC)=O)C(OCC)=O)(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)=CC=1.[O:41]1[C:46](=[O:47])[CH2:45][O:44][CH2:43][C:42]1=[O:48]>O1CCOCC1>[C:42]([OH:48])(=[O:2])[CH2:43][O:44][CH2:45][C:46]([OH:41])=[O:47]

Participants

4

Reactant 2

HCID 782321,4-Dioxane-2,6-dioneHCID 15539820Diethyl 2-[(4,4',4''-trimethoxytrityl)oxymethyl]-2-hydroxymethylmalonate

Product 1

HCID 8088Diglycolic AcidYield 574.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Referring to scheme 2, a mixture of 1 (1.11 g, 2.0 mmol), 1,4-dioxane-2,6-dione (0.70 g, 6.0 mmol), Py (5 mL), and dioxane (5 mL) was kept overnight at room temperature. The solvent was evaporated and the residue was dissolved in ethyl acetate (50 mL). The solution was washed with 2 M aqueous triethylammonium acetate (5×10 mL) and water (5×10 mL), dried over Na2SO4. The extract was evaporated to give crude monoester of 2 with diglycolic acid (1.54 g; triethylammonium salt) as a solid foam in a quantitative yield.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washThe solution was washed with 2 M aqueous triethylammonium acetate (5×10 mL) and water (5×10 mL)
  4. dry with materialdried over Na2SO4
  5. customThe extract was evaporated

Sources & evidence

ORD record
ord-39083922193949da83dfd0e766963372
Source dataset
uspto-grants-2004_11
Patent number
US06825338B2

Reaction notes

Loading…