2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 58231456, compound

HRID 2381264Notes

Reaction equation

HRID 2381264 reaction equation
CC1(C)[O:9][C:7](=[O:8])[CH2:6][C:4](=O)O1.[Cl:11][C:12]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[C:13]=1C=O>CCN(CC)CC.C(O)=O>[Cl:11][C:12]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[C:13]=1[CH2:4][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 53144572,4,6-Trichlorobenzaldehyde

Product 1

HCID 58231456HCID 58231456, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 11084032Triethylammonium formateSolvent

Conditions

Temperature
120 °C

Procedure

Meldrum's acid (2.06 g, 14.32 mmoles) was added to TEAF (7.05 ml) at ambient temperature under stirring and the reaction mixture was kept under nitrogen atmosphere. After 10 min 2,4,6-trichloro benzaldehyde (3 g, 14.32 mmoles) was added to the reaction mixture. It was then refluxed at 120° C. for 3 hrs. On completion of the reaction, the mixture was cooled at ambient and was poured into ice water (50 ml). Then aq. layer was extracted with ethyl acetate (3×80 ml), the combined organic layer was washed with brine (40 ml) and dried over sodium sulphate. Organic layer was concentrated under vacuum. 3.10 g (86.0% of theory) of 3-(2,4,6-trichloro-phenyl)-propionic acid was obtained in form of a white solid.

Workup

  1. customOn completion of the reaction
  2. temperaturethe mixture was cooled at ambient and
  3. extractionThen aq. layer was extracted with ethyl acetate (3×80 ml)
  4. washthe combined organic layer was washed with brine (40 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationOrganic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-35ab6ea9ddde415597b606fac007c2ef
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

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