Ethylene Glycol → 2-(4-Bromophenyl)-2-butyl-1,3-dioxolane

HRID 250511Notes

Reaction equation

HRID 250511 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[CH2:14](O)[CH2:15][OH:16]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:9][CH2:10][CH2:11][CH3:12])[O:16][CH2:15][CH2:14][O:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 817174'-Bromovalerophenone

Product 1

HCID 114261402-(4-Bromophenyl)-2-butyl-1,3-dioxolaneYield 92%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 4′-bromovalerophenone (2.41 g, 10 mmol) in benzene (60 ml) was added ethylene glycol (2.0 ml, 36 mmol), p-toluenesulfonic acid monohydrate (100 mg, 0.53 mmol) and the mixture refluxed under nitrogen in a Dean-Stark apparatus for 16 h. The reaction mixture was washed with sodium bicarbonate solution (5%, 50 ml), brine (1×50 ml), dried (Na2SO4) and evaporated to give 2-(4-bromophenyl)-2-butyl-1,3-dioxolane (11) as a clear oil (2.61 g, 92%). 1H nmr (CDCl3, 300 MHz) 0.88, t (6.9 Hz), H4″; 1.2-1.4, m, H2″,3″; 1.88, m, H1″; 3.7-3.8, m, CH2O; 4.0-4.1, m, CH2O; 7.34, d (8.4 Hz), H2′,6′; 7.49, d (8.4 Hz), H3′,5′. ESI (+ve) MS m/z 285/287 (M+H, 8%).

Workup

  1. temperaturethe mixture refluxed under nitrogen in a Dean-Stark apparatus for 16 h
  2. washThe reaction mixture was washed with sodium bicarbonate solution (5%, 50 ml), brine (1×50 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-63864dc218214568bd0d9ddf1542da89
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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