Ethylene Glycol → Methyl (2-ethyl-1,3-dioxolan-2-yl)acetate

HRID 2200569Notes

Reaction equation

HRID 2200569 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:10](O)[CH2:11][OH:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:8]([C:2]1([CH2:3][C:4]([O:6][CH3:7])=[O:5])[O:12][CH2:11][CH2:10][O:1]1)[CH3:9]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 121699Methyl 3-oxovalerate

Product 1

HCID 13085711Methyl (2-ethyl-1,3-dioxolan-2-yl)acetateYield 42.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 3-oxopentanoate (3 g, 23.1 mmol) in toluene (30 mL) was added ethane-1,2-diol (3 mL, 70.2 mmol) and p-toluenesulfonic acid (500 mg, 2.91 mmol), the resulting mixture was stirred at 120° C. overnight. Then the mixture was concentrated and partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution. The phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate; then it was filtered and concentrated to give methyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetate (1.7 g, 42.5%) as yellow oil which was used without purification. Product tlc [petroleum ether/ethyl acetate (15:1) developed with iodine, Rf 0.6]

Workup

  1. concentrationThen the mixture was concentrated
  2. custompartitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationthen it was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e9c4242b5d034850ac3265d3d78b1575
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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