p-Toluenesulfonic acid → HCID 66996901, compound

HRID 2369176Notes

Reaction equation

HRID 2369176 reaction equation
[C:1]([OH:6])(=[O:5])[C@H:2]([CH3:4])[OH:3].[C:7]1([CH3:17])[CH:12]=CC(S(O)(=O)=O)=C[CH:8]=1>CCCCC>[CH3:4][CH:2]1[O:3][CH:8]([CH:7]([CH3:17])[CH3:12])[O:5][C:1]1=[O:6]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 107689L-Lactic Acid

Product 1

HCID 66996901HCID 66996901, compoundYield 869,816.188%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

43.6 g (0.60 mol) of isobutyl aldehyde, 62.5 g (0.55 mol) of L-lactic acid, and 1.06 g (0.05 mmol) of p-toluene sulfonic acid were dissolved in 50 ml of n-pentane, and the mixture was refluxed for 8 hours in a 500-ml flask attached to a reflux condenser comprising a Dean-Stark fractionator. After the reaction, the reaction mixture was neutralized and washed with a sodium bicarbonate aqueous solution, followed by extraction with ether. Thereafter, the extract was dried with anhydrous magnesium sulfate. Thereafter, ether was distilled off, thereby giving 62.7 g (yield=79.2%) of 5-methyl-2-isopropyl-1,3-dioxolan-4-one as a diastereomer mixture.

Workup

  1. temperaturethe mixture was refluxed for 8 hours in a 500-ml flask
  2. customattached to a reflux condenser
  3. customAfter the reaction
  4. washwashed with a sodium bicarbonate aqueous solution
  5. extractionfollowed by extraction with ether
  6. dry with materialThereafter, the extract was dried with anhydrous magnesium sulfate
  7. distillationThereafter, ether was distilled off

Sources & evidence

ORD record
ord-43f1a502eae24b6eb0505e6ca128d5f5
Source dataset
uspto-grants-2014_04
Patent number
US08703890B2

Reaction notes

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