Ethylene Glycol → 1,3-Dioxolane, 2-(2-bromo-5-methoxyphenyl)-

HRID 1967432Notes

Reaction equation

HRID 1967432 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:12](O)[CH2:13][OH:14].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]1[O:14][CH2:13][CH2:12][O:5]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 3444802-Bromo-5-methoxybenzaldehyde

Product 1

HCID 111845031,3-Dioxolane, 2-(2-bromo-5-methoxyphenyl)-Yield 103.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound 19 (50.0 g, 0.23 mol) in toluene (650 mL) were added ethylene glycol (14.2 mL, 0.26 mol) and camphorsulfonic acid (10.7 g, 46 mmol). The reaction solution was heated under reflux with a Dean-Stark trap for 6 h and then cooled to room temperature and diluted with ethyl acetate (300 mL). The resulting solution was washed with aqueous saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo to give Compound 20 (61.5 g, quantitative) as a yellow oil: 1H NMR (CDCl3, 500 MHz) δ 7.44 (d, J=8.5 Hz, 1H), 7.15 (d, J=3.5 Hz, 1H), 6.79 (dd, J=8.5, 3.0 Hz, 1H), 6.04 (s, 1H), 4.18-4.06 (m, 4H), 3.81 (s, 3H).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux with a Dean-Stark trap for 6 h
  3. washThe resulting solution was washed with aqueous saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90ba0b4bb6364c3c9be2d04436426ca5
Source dataset
uspto-grants-2013_04
Patent number
US08420811B2

Reaction notes

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