Ethylene Glycol → 2-(4-Bromobutyl)-2-methyl-1,3-dioxolane

HRID 2064930

Reaction equation

HRID 2064930 reaction equation
N#N.[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:10])[CH3:9].[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCOCC>[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1([CH3:9])[O:13][CH2:12][CH2:11][O:10]1

Participants

8

Reactant 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 6101p-Toluenesulfonic acidHCID 250616-Bromohexan-2-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 5600132-(4-Bromobutyl)-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus under inert atmosphere (N2), a solution of 6-bromo-hexan-2-one (3.34 g, 18.65 mmol) in toluene (71.3 mL) was treated with ethylene glycol (10.4 mL, 186.92 mmol) and TsOH (35 mg, 0.19 mmol). The reaction mixture was heated to reflux for 3 h, allowed to cool to rt and sat. aq. NaHCO3 (100 mL) and ether (100 mL) were added and the aq. phase was washed with water (2×100 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound. 1H NMR (400 MHz, CDCl3) δ 1.34 (s, 3H), 1.50-1.65 (m, 2H), 1.65-1.75 (m, 2H), 1.84-1.98 (m, 2H), 3.43 (t, J=6.8 Hz, 2H), 3.90-4.04 (m, 4H).

Workup

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 3 h
  4. washthe aq. phase was washed with water (2×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-844605ff2f0a4743b715a881eff14e13
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Linked notes

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