Water → 2,2-Dimethylmalonic acid mono-(2,2-dimethylpropyl)ester

HRID 2089663

Reaction equation

HRID 2089663 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][O:4][C:5](=[O:16])[C:6]([CH3:15])([CH3:14])[C:7]([O:9]C(C)(C)C)=[O:8].C(OCC)(=O)C.O>ClCCl.C(O)(C(F)(F)F)=O>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][O:4][C:5](=[O:16])[C:6]([CH3:15])([CH3:14])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 866773992,2-Dimethylmalonic acid t-butyl ester (2,2-dimethylpropyl)ester

Product 1

HCID 183316662,2-Dimethylmalonic acid mono-(2,2-dimethylpropyl)esterYield 92.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of the obtained 2,2-dimethylmalonic acid t-butyl ester (2,2-dimethylpropyl)ester (12 g) in dichloromethane (100 mL), TFA (20 mL) was added, and the resulting mixture was stirred at room temperature for 3 hours. Ethyl acetate and water were added to the mixture. After shaking the resulting mixture, the organic layer was collected, sequentially washed with water and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and toluene was added to the filtrate obtained, after which the resulting mixture was concentrated under reduced pressure to obtain the captioned compound (8.7 g).

Workup

  1. stirringAfter shaking the resulting mixture
  2. customthe organic layer was collected
  3. washsequentially washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. additiontoluene was added to the filtrate
  7. customobtained
  8. concentrationafter which the resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-52d169c4c3d346a2b900021cddd8b91e
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Linked notes

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