Ethylene Glycol → HCID 11160986, compound

HRID 250518Notes

Reaction equation

HRID 250518 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:27](O)[CH2:28][OH:29]>C1(C)C=CC=CC=1>[CH2:9]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[O:29][CH2:28][CH2:27][O:15]1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 13496998HCID 13496998, compound

Product 1

HCID 11160986HCID 11160986, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-methylphenyl)-1-heptanone (200 mg, 0.980 mmol), p-toluenesulfonic acid (17 mg, 0.098 mmol) and ethylene glycol (0.16 mL, 2.9 mmol) in dry toluene (10 mL) was heated at reflux with a Dean-Stark apparatus under nitrogen for 24 h. The mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo. The residue was taken up in ether (20 mL) and the solution was washed with saturated sodium carbonate solution (2×10 mL) and brine (1×10 mL), then dried (Na2SO4) and concentrated under reduced pressure. Flash column chromatography of the residue, eluting with dichloromethane/hexane (1:2) afforded 2-hexyl-2-(4-methylphenyl)-1,3-dioxolane (19) as a tan-coloured oil (162 mg, 67%). 1H nmr (200 Mz, CDCl3) 0.80-0.92 (m, 3H, CH2CH3), 1.18-1.40 [m, 8H, (CH2)4], 1.84-1.89 (m, 2H, CCH2), 2.34 (s, 3H, ArCH3), 3.73-3.81 (m, 2H, OCH2), 3.94-4.02 (m, 2H, OCH2), 7.13 (d, J=8.2 Hz, 2H, 2×ArH), 7.32 (d, J=8.2 Hz, 2H, 2×ArH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark apparatus under nitrogen for 24 h
  3. customthe solvent was evaporated in vacuo
  4. washthe solution was washed with saturated sodium carbonate solution (2×10 mL) and brine (1×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. washFlash column chromatography of the residue, eluting with dichloromethane/hexane (1:2)

Sources & evidence

ORD record
ord-4c3422f8832047fe96d96af5f258b19b
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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