Potassium Hydroxide → HCID 67076941, compound

HRID 1348595Notes

Reaction equation

HRID 1348595 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5](=[O:17])[CH:6]([CH2:11][CH:12]1[O:16][CH2:15][CH2:14][O:13]1)[C:7]([O:9]C)=[O:8]>CO>[CH3:3][O:4][C:5](=[O:17])[CH:6]([CH2:11][CH:12]1[O:16][CH2:15][CH2:14][O:13]1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67076882HCID 67076882, compound

Product 1

HCID 67076941HCID 67076941, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1.03 g (18 mmol) potassium hydroxide in 15 ml methanol were added 4.00 g (18 mmol) (1,3-dioxolan-2-ylmethyl)propanedioic acid dimethyl ester. After stirring overnight at 85° C. the solvent was distilled off. The residue was extracted with water/ethylacetate. The aqueous phase was then acidified with concentrated hydrochloric acid. Extraction with ethylacetate gave 2.11 g (56%) 2-[1,3]dioxolan-2-ylmethyl-malonic acid monomethyl ester as light yellow oil, 1H-NMR (ppm, CDCl3) δ 2.38–2.42 (m, 2H), 3.65 (t, 1H, J=6.9 Hz), 3.77 (s, 3H), 3.79–3.97 (m, 4H), 5.03 (t, 1H, J=3.6 Hz).

Workup

  1. distillationwas distilled off
  2. extractionThe residue was extracted with water/ethylacetate
  3. extractionExtraction with ethylacetate

Sources & evidence

ORD record
ord-efd143c78d7641f8b200def76dd1b195
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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