Ethylene Glycol → 2-(5-Bromo-2-methylphenyl)-1,3-dioxolane

HRID 1629723Notes

Reaction equation

HRID 1629723 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:7]2[O:13][CH2:12][CH2:11][O:8]2)[CH:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 104202895-Bromo-2-methylbenzaldehyde

Product 1

HCID 583744502-(5-Bromo-2-methylphenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of INT 30 (17.3 g, 87 mmol) in toluene (505 mL) was added ethane-1,2-diol (24.3 mL, 436 mmol) followed by p-toluenesulfonic acid monohydrate (0.83 g, 4.36 mmol). The reaction mixture was stirred at 130° C. for 21 hours. The mixture was washed with saturated aqueous NaHCO3 (2×) and brine (2×). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by Kugelrohr distillation to give INT 31.

Workup

  1. washThe mixture was washed with saturated aqueous NaHCO3 (2×) and brine (2×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. distillationThe residue was purified by Kugelrohr distillation
  6. customto give INT 31

Sources & evidence

ORD record
ord-5a0c0b5fb72943c9816dc6ef20695081
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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