p-Toluenesulfonic acid → HCID 54124038, compound

HRID 224732Notes

Reaction equation

HRID 224732 reaction equation
[C:1]1(C)[CH:6]=CC(S(O)(=O)=O)=C[CH:2]=1.[OH:12][C@:13]([CH3:21])([CH2:19][OH:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>>[CH3:2][C:1]1([CH3:6])[O:12][C@@:13]([CH3:21])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:19][O:20]1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53737198Ethyl (2R)-2,3-dihydroxy-2-methylpropanoate

Product 1

HCID 54124038HCID 54124038, compoundYield 2,049.4%

Procedure

500 mg of p-toluenesulfonic acid were added to 10.7 g of ethyl (R)-2,3-dihydroxy-2-methylpropionate, dissolved in 35 ml of dry, freshly distilled 2,2-dimethoxypropane, and the mixture was stirred at room temperature overnight. The excess dimethoxypropane was removed at 45°/12 mmHg and the residue was vigorously stirred for 30 minutes with 5 ml of 1-N sodium bicarbonate. Then, 150 ml of ether were added thereto and the aqueous phase was separated. The ether solution was washed with saturated brine and then dried over sodium sulfate. After evaporation of the solvent, the product was distilled and there were obtained 11.2 g of ethyl (R)-2,2,4-trimethyl-1,3-dioxolan-4-carboxylate in the form of a colorless liquid; boiling point 81°/15 mmHg.

Workup

  1. dissolutiondissolved in 35 ml
  2. customof dry
  3. customThe excess dimethoxypropane was removed at 45°/12 mmHg
  4. stirringthe residue was vigorously stirred for 30 minutes with 5 ml of 1-N sodium bicarbonate
  5. additionThen, 150 ml of ether were added
  6. customthe aqueous phase was separated
  7. washThe ether solution was washed with saturated brine
  8. dry with materialdried over sodium sulfate
  9. customAfter evaporation of the solvent
  10. distillationthe product was distilled

Sources & evidence

ORD record
ord-b283fb2549c34dab868f0614f7e0bd54
Source dataset
uspto-grants-1980_11
Patent number
US04234490

Reaction notes

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