Sodium Carbonate → 2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

HRID 1168046Notes

Reaction equation

HRID 1168046 reaction equation
[CH2:1]([OH:7])[C@@H:2]([OH:6])[CH2:3][CH2:4][OH:5].O.[C:9]1(C)[CH:14]=CC(S(O)(=O)=O)=C[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[OH:5][CH2:4][CH2:3][C@H:2]1[CH2:1][O:7][C:9]([CH3:14])([CH3:10])[O:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 6409971,2,4-Butanetriol, (2S)-

Product 1

HCID 110518052-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-olYield 6,655.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (s)-1,2,4-butanetriol (0.842 g, 7.9 mmol) dissolved in acetone (12 ml) was added p-toluenesulfonic acid hydrate (20 mg) and the mixture was stirred for 21 hours at room temperature. Sodium carbonate (20 mg) was added to the mixture. After stirring for 1 hour, the mixture was filtered and condensed in vacuo to give (S)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (1.023 g, yield 88%).

Workup

  1. stirringAfter stirring for 1 hour
  2. filtrationthe mixture was filtered
  3. customcondensed in vacuo

Sources & evidence

ORD record
ord-c73ade3dfee1420f86b1d1f63f2b2fe9
Source dataset
uspto-grants-2003_09
Patent number
US06620977B1

Reaction notes

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