Hydrochloric Acid → Butanoic acid, 4-(2-methoxyethoxy)-3-oxo-, ethyl ester

HRID 2233889Notes

Reaction equation

HRID 2233889 reaction equation
C[C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])O1.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16]C(Cl)=O.Cl>N1C=CC=CC=1>[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][C:4](=[O:9])[CH2:5][C:6]([O:7][CH2:2][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 70103382-(2-Methoxyethoxy)acetyl chloride

Product 1

HCID 2759572Butanoic acid, 4-(2-methoxyethoxy)-3-oxo-, ethyl esterYield 63.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,2-Dimethyl-1,3-dioxane-4,6-dione (1.72 g) was suspended in anhydrous pyridine (20 ml) and cooled to 0° C. (2-methoxyethoxy)acetyl chloride (2 g) was added slowly. The mixture was stirred at room temperature for 3 h. The mixture was poured into 2 N HCl (30 ml) and extracted with DCM (×3). The combined organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The orange oil was dissolved in EtOH (20 ml) and was refluxed for 7 h. The solvent was removed in vacuo and the brown oil was Kugelrohr distilled affording the title compound as a colourless oil (1.55 g).

Workup

  1. additionwas added slowly
  2. extractionextracted with DCM (×3)
  3. washThe combined organic phase was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe orange oil was dissolved in EtOH (20 ml)
  7. temperaturewas refluxed for 7 h
  8. customThe solvent was removed in vacuo
  9. distillationdistilled

Sources & evidence

ORD record
ord-0c25be44d8294cc386cc15fc5058da09
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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