p-Toluenesulfonic acid → (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropan-1-ol

HRID 876497Notes

Reaction equation

HRID 876497 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:7][OH:8])[C@@H:3]([OH:6])[CH2:4][OH:5].[CH3:10][C:11]1C=CC(S(O)(=O)=O)=C[CH:12]=1>CC(C)=O>[CH3:10][C:11]1([CH3:12])[O:6][C@H:3]([C:2]([CH3:9])([CH3:1])[CH2:7][OH:8])[CH2:4][O:5]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acid2×HCID 10988310(R)-3,3-dimethylbutane-1,2,4-triol

Product 1

HCID 12241295(R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropan-1-olYield 9,756.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(R)-3,3-dimethylbutane-1,2,4-triol (2.7 g, 20 mmol) and 4-methylbenzenesulfonic acid (0.017 g, 0.10 mmol) were added to 25 mL of acetone and catalytic 4-methylbenzenesulfonic acid (0.017 g, 0.10 mmol) and stirred overnight at ambient temperature. The solution was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with aqueous Na2CO3, dried over MgSO4 and filtered. The filtrate was concentrated to provide 1.7 g of the desired product as a clear oil.

Workup

  1. customThe solution was evaporated
  2. additionto the residue was added ethyl acetate
  3. washThe organic layer was washed with aqueous Na2CO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2e9ae70a1cb946d9b1a4be9da94f1d5e
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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