Ethylene Glycol → 2-Indanyl-4-methyl-1,3-dioxolane

HRID 1251569Notes

Reaction equation

HRID 1251569 reaction equation
[CH:1]1([CH:10]=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1C2C(=CC=CC=2)C[CH:13]1[CH:21]=[O:22].[CH2:23](O)CO>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH:1]1([CH:10]2[O:22][CH:21]([CH3:13])[CH2:23][O:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 111161982,3-dihydro-1H-indene-1-carbaldehydeHCID 117447712,3-Dihydro-1H-indene-2-carbaldehyde

Product 1

HCID 113216642-Indanyl-4-methyl-1,3-dioxolane

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 297 grams of a mixture of 70% indancarbaldehyde and 30% indan-2-carbaldehyde, 300 grams of ethylene glycol, 6 grams of p-toluenesulfonic acid and 300 grams of toluene are heated 2 hours at reflux using a Dean-Stark trap to separate water. The mixture is cooled and washed with 200 milliliters of a 5 weight % sodium carbonate solution. The organic layer is distilled to provide 321 grams of 2-indanyl-4-methyl-1,3-dioxolane (b.p.121° C. at 3 mm).

Workup

  1. temperatureat reflux
  2. customto separate water
  3. temperatureThe mixture is cooled
  4. washwashed with 200 milliliters of a 5 weight % sodium carbonate solution
  5. distillationThe organic layer is distilled

Sources & evidence

ORD record
ord-6840ddc9caaa4467bce4e2cf188904e6
Source dataset
uspto-grants-2002_01
Patent number
US06342612B1

Reaction notes

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