Ethylene Glycol → Acetoacetic Acid

HRID 1025683Notes

Reaction equation

HRID 1025683 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(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

5

Reactant 2

HCID 174Ethylene GlycolHCID 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 TMSC1 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-6c2ac0b41b9a4b67b9997d9369cbc40f
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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