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

HRID 604844Notes

Reaction equation

HRID 604844 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:10])[O:13][CH2:12][CH2:11][O:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 165023'-Bromoacetophenone

Product 1

HCID 109992182-(3-Bromophenyl)-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

30.1 g (151 mmol) of (3-bromophenyl)methyl ketone and 13.8 g (222 mmol) of ethylene glycol are dissolved in 120 mL of benzene, mixed with 60 mg of 4-toluenesulphonic acid and boiled under reflux at a water separator (Dean-Stark apparatus) until no more water is separated off. The reaction solution is washed with 50 mL of a 0.5 M NaHCO3 solution, the organic phase is separated off and dried over anhydrous MgSO4. After removal of the benzene in a rotary evaporator, the residue becomes the product with a purity (GC) of 97% in nearly quantitative yield as colorless oily liquid. C10H11O2Br.

Workup

  1. customis separated off
  2. washThe reaction solution is washed with 50 mL of a 0.5 M NaHCO3 solution
  3. customthe organic phase is separated off
  4. dry with materialdried over anhydrous MgSO4
  5. customAfter removal of the benzene
  6. customin a rotary evaporator

Sources & evidence

ORD record
ord-f8b60560772c45c29d4319abe3ba1a7c
Source dataset
uspto-grants-2011_03
Patent number
US07910744B2

Reaction notes

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