Ethylene Glycol → Acetoacetic Acid

HRID 1809844Notes

Reaction equation

HRID 1809844 reaction equation
[O:1]=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:13](O)[CH2:14][OH:15].C[Si](Cl)(C)C>C(Cl)Cl>[O:1]1[CH2:13][CH2:14][O:15][C:2]1([CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH3:8][C:2]([CH2:3][C:4]([OH:6])=[O:5])=[O:1]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 74591Dimethyl 3-oxoglutarate

Product 2

HCID 96Acetoacetic AcidYield 100%HCID 228900Dimethyl 2,2'-(1,3-dioxolane-2,2-diyl)diacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4.2 g (24 mmol) of dimethyl 3-oxopentanedioate and 2.7 ml (48 mmol) of ethylene glycol in 50 mL of methylene chloride was added 12 mL (96 mmol) of TMSCl at room temperature. The reaction mixture was stirred at 50° C. for 3 days. The reaction was quenched with saturated NaHCO3 aqueous solution. The aqueous layer was extracted with ether. The combined organic layers were washed with brine, dried over Na2SO4, evaporated under reduced pressure. Chromatography on silica gel gave the desired product, dimethyl dioxolane-2,2-diyl)diacetate (2.6 g, 12 mmol, yield: 50%): MS (m/e): 219 (M+1)+.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 aqueous solution
  2. extractionThe aqueous layer was extracted with ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-909979aa45a243728f6a6ae156f9d617
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

Loading…