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

HRID 42750

Reaction equation

HRID 42750 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 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) δ1.34 (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-1f37e5b7d2814e2bb7eb2867e6bdecb9
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Linked notes

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