Ethylene Glycol → HCID 11483263, compound

HRID 250528Notes

Reaction equation

HRID 250528 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:19](O)[CH2:20][OH:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:21][CH2:20][CH2:19][O:18]2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 35225871-(3,5-Dimethoxyphenyl)heptan-1-one

Product 1

HCID 11483263HCID 11483263, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(3,5-Dimethoxyphenyl)heptan-1-one (200 mg, 0.80 mmol), ethylene glycol (173 mg, 2.80 mmol) and a catalytic amount of p-toluenesulfonic acid monohydrate were refluxed in toluene (25 mL) overnight in a Dean-Stark apparatus. The reaction mixture was then concentrated and the residue dissolved in chloroform (50 mL) and washed with saturated sodium bicarbonate solution (2×25 mL) then brine (1×25 mL). The organic phase was dried (Na2SO4) and evaporated to give 2-(3,5-dimethoxyphenyl)-2-hexyl-1,3-dioxolane (41) as a light yellow oil (213 mg, 90%). 1H NMR (CDCl3, 300 MHz): δ 0.94, t (6.5 Hz), CH3; 1.31, m, methylene envelope; 1.89, m, CH2; 3.79-3.83, m, 2×OMe, OCH2; 4.04, m, OCH2; 6.46, m, H4′; 6.63, m, H2′,6′. ESI (+ve) MS: m/z 295 (M+H, 62%).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue dissolved in chloroform (50 mL)
  3. washwashed with saturated sodium bicarbonate solution (2×25 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ef7baf6bcf034617af8e330501d2e49b
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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