Ethylene Glycol → HCID 57429413, compound

HRID 2369778Notes

Reaction equation

HRID 2369778 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:16][CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH2:27][CH:28]=O)[CH3:26])[CH:20]=1)[CH3:18]>C1CCCCC1>[CH:17]([C:19]1[CH:20]=[C:21]([CH:25]([CH3:26])[CH2:27][CH:28]2[O:4][CH2:1][CH2:2][O:3]2)[CH:22]=[CH:23][CH:24]=1)([CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 86209Florhydral2×

Product 1

HCID 57429413HCID 57429413, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Ethylene glycol (18 mL, 0.32 mol, 1.2 eq), paratoluene sulfonic acid (400 mg, 1% w/w) and cyclohexane (50 mL) were charged into a 1 L three-necked round-bottom flask, equipped with a dean and stark, a reflux condenser and a mechanical stirrer. Florhydral™ 3-(3-isopropylphenyl)butanal, 49.3 g, 0.26 mol) was added dropwise at ambient temperature. The stirred mixture was then heated for 3 h at reflux. The reaction mixture was cooled at ambient temperature and washed water (2×100 mL), dried over magnesium sulphate and concentrated. The resulting crude product was distilled with a Vigreux column (7.2 mBar, 146° C.), to give 2-[2-(3-isopropylphenyl)propyl]-1,3-dioxolane (239 g, gc purity>98%; yield 97%).

Workup

  1. customequipped with a dean
  2. temperatureThe stirred mixture was then heated for 3 h
  3. temperatureat reflux
  4. washwashed water (2×100 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. distillationThe resulting crude product was distilled with a Vigreux column (7.2 mBar, 146° C.)

Sources & evidence

ORD record
ord-a9ecb8ca7cb04a21ac02f1495d955dd6
Source dataset
uspto-grants-2014_04
Patent number
US08709994B2

Reaction notes

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