Ethylene Glycol → HCID 18690801, compound

HRID 741579Notes

Reaction equation

HRID 741579 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([CH:14]=[O:15])[CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[CH2:16](O)[CH2:17][OH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1CCCCC1>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([CH:14]1[O:18][CH2:17][CH2:16][O:15]1)[CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 18350561HCID 18350561, compound

Product 1

HCID 18690801HCID 18690801, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A mixture of 5-tert-butyl-2-indancarbaldehyde (ex. 4; 9.8mmole), ethyleneglycol (6.1 g, 98 mmole) and p-toluenesulfonic acid (95 mg, 0.5 mmole) in cyclohexane (25 ml), was heated to reflux (80°) during 3 h with a Dean-Stark type trap. The cooled mixture was poured on ether and aq. sat. NaHCO3, and the organic phase was washed with aq. sat. NaHCO3, dried over K2CO3 and concentrated. After bulb-to-bulb distillation, the desired dioxolane was obtained.

Workup

  1. temperaturewas heated
  2. temperatureto reflux (80°) during 3 h with a Dean-Stark type trap
  3. washthe organic phase was washed with aq. sat. NaHCO3
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated
  6. distillationAfter bulb-to-bulb distillation

Sources & evidence

ORD record
ord-e40453907c9c4273b7e73c90285edd2b
Source dataset
uspto-grants-1996_09
Patent number
US05552379

Reaction notes

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