Ethylene Glycol → HCID 12622466, compound

HRID 1253315Notes

Reaction equation

HRID 1253315 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].[CH2:13](O)[CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[O:15][CH2:14][CH2:13][O:4]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 12622466HCID 12622466, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-bromo-1-(4'-methoxy-phenyl)-ethanone (20 g, 87 mmol), ethylene glycol (54 g, 870 mmol), para-toluenesulfonic acid hydrate (1.7 g, 8.7 mmol) and benzene (50 ml) are heated and stirred together for 5 h in a flask beneath a Dean-Stark trap. The reaction mixture is added dropwise to a well stirred saturated sodium carbonate solution (0.4 l) and extracted with ethyl ether (3×70 ml). The combined organic extract is washed with a 2% sodium hydrogen carbonate solution, dried (Na2CO3) and filtered. The solvent is evaporated under reduced pressure to give 2-bromomethyl-2-(4'-methoxy-phenyl)-1,3-dioxolane (23.5 g, 86 mmol; yield: 99%).

Workup

  1. extractionextracted with ethyl ether (3×70 ml)
  2. extractionThe combined organic extract
  3. washis washed with a 2% sodium hydrogen carbonate solution
  4. dry with materialdried (Na2CO3)
  5. filtrationfiltered
  6. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-3744e87f217f45a69a52335cdaccf3fd
Source dataset
uspto-grants-1988_05
Patent number
US04748253

Reaction notes

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