Ethylene Glycol → 2-(3-Bromo-4-methoxyphenyl)-1,3-dioxolane

HRID 1662743Notes

Reaction equation

HRID 1662743 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:14][CH2:13][CH2:12][O:6]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 986623-Bromo-4-methoxybenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 179350472-(3-Bromo-4-methoxyphenyl)-1,3-dioxolaneYield 92.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A solution of 53.0 g of 3-bromo-4-methoxy benzaldehyde, 18.4 g of ethylene glycol, and 4.24 g of p-toluene sulfonic acid/1 hydrate in benzene was refluxed for 5 hours while taking water out of the system. After the mixture was cooled, the reaction solution was poured into a saturated aqueous solution of NaHCO3, liquid separation was performed, and the aqueous layer was extracted with benzene. The combined organic layer was washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (Chromatorex NH; mobile phase: EtOAc/n-hexane=1/9; v/v) to obtain 59.1 g of the title compound (colorless oil) was obtained.

Workup

  1. temperatureAfter the mixture was cooled
  2. extractionthe aqueous layer was extracted with benzene
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (Chromatorex NH; mobile phase: EtOAc/n-hexane=1/9; v/v)

Sources & evidence

ORD record
ord-db12b2397d474176af4247f789900e6a
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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