Acetone → HCID 12231420, compound

HRID 2183996Notes

Reaction equation

HRID 2183996 reaction equation
[OH:1][C:2]([CH3:8])([CH2:6][OH:7])[C:3](=[O:5])[CH3:4].[CH3:9][C:10]([CH3:12])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCCC(C)C>[CH3:9][C:10]1([CH3:12])[O:1][C:2]([C:3](=[O:5])[CH3:4])([CH3:8])[CH2:6][O:7]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 10997012HCID 10997012, compound

Product 1

HCID 12231420HCID 12231420, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Procedure

A mixture of 3,4-dihydroxy-3-methylbutan-2-one (4.13 g, 35 mmol), acetone (25 ml) and p-toluenesulfonic acid monohydrate (33 mg, 0.18 mmol) in isohexane (75 ml) was heated in a Dean-Stark apparatus for 10 h. The solvent was removed by distillation at atmospheric pressure and the residue purified by chromatography on silica gel. Elution with 50% ether in isohexane afforded 1-(2,2,4-trimethyl-[1,3]dioxolan-4-yl)ethanone as a pale yellow liquid (5.1 g, 92%): δH (360 MHz, d6-DMSO) 1.29 (3H, s), 1.34 (3H, s), 1.36 (3H, s), 2.20 (3H, s), 3.69 (1H, d, J 9), 4.18 (1H, d, J 9).

Workup

  1. temperaturewas heated in a Dean-Stark apparatus for 10 h
  2. customThe solvent was removed by distillation at atmospheric pressure
  3. customthe residue purified by chromatography on silica gel
  4. washElution with 50% ether in isohexane

Sources & evidence

ORD record
ord-330f8caf9b2e44f4a21164d8f5a6e48b
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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