p-Toluenesulfonic acid → 2-Formyl-5,5-dimethyl-1,3-dioxane

HRID 1784126Notes

Reaction equation

HRID 1784126 reaction equation
[CH:1]([CH:3]=[O:4])=[O:2].[CH3:5][C:6]([CH3:11])([CH2:9]O)[CH2:7][OH:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O-]S([O-])(=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[CH:1]([CH:3]1[O:8][CH2:7][C:6]([CH3:11])([CH3:9])[CH2:5][O:4]1)=[O:2]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 7860GlyoxalHCID 24436Sodium SulfateHCID 31344Neopentyl glycolHCID 516892Sodium Bicarbonate

Product 1

HCID 108555902-Formyl-5,5-dimethyl-1,3-dioxaneYield 4.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of glyoxal (10.0 g of 40 wt. % aqueous solution, 0.070 mol), 2,2-dimethyl-1,3-propanediol (7.28 g, 0.070 mol) and p-toluenesulfonic acid (0.260 g, 1.36 mmol) in benzene (140 mL) was refluxed for 4 h in a flask fitted with a Soxhlet extractor containing Na2SO4. Then the reaction mixture was treated with solid NaHCO3 (0.250 g, 2.90 mmol) and filtered. The filtrate was concentrated and vacuum distilled (Kugelrohr) to afford a colorless liquid (413 mg, 4%). The 1H NMR spectrum was consistent with the data reported in a patent.19 This reactive compound was used immediately in the next reaction.

Workup

  1. temperaturewas refluxed for 4 h in a flask
  2. customfitted with a Soxhlet extractor
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. distillationvacuum distilled (Kugelrohr)

Sources & evidence

ORD record
ord-4a1c97c9bb4c4b699f0f6ce0d76f9695
Source dataset
uspto-grants-2009_03
Patent number
US07501507B2

Reaction notes

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