Citric Acid → 2,2,5-Trimethyl-1,3-dioxolane-4-carboxylato

HRID 2426963Notes

Reaction equation

HRID 2426963 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][CH:5]([C:7]([O:9]C)=[O:8])[CH:4]([CH3:11])[O:3]1.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH3:1][C:2]1([CH3:12])[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH:4]([CH3:11])[O:3]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 4523932HCID 4523932, compound

Product 1

HCID 3152572,2,5-Trimethyl-1,3-dioxolane-4-carboxylato

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate (1 mL) in tetrahydrofuran (10 mL) was added 1N aqueous lithium hydroxide (10 mL) and the mixture was stirred at room temperature for an hour. The reaction mixture was poured into iced 10% citric acid, then extracted with ethyl acetate. The obtained organic layer was washed with brine, dried and concentrated to give the title compound (425 mg) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe obtained organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8f0227e35e448aabe9e03bfdfe5e318
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

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