Ethylene Glycol → HCID 11301269, compound

HRID 1990844Notes

Reaction equation

HRID 1990844 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH:5]=[O:6].[CH2:11](O)[CH2:12][OH:13]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:13][CH2:12][CH2:11][O:6]2)[CH:7]=[C:8]([Br:10])[CH:9]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 6220773,5-Dibromobenzaldehyde

Product 1

HCID 11301269HCID 11301269, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 3,5-dibromo-benzaldehyde (20.0 g, 75.8 mmol, 1.0 equiv; [CAS RN 56990-02-4]), ethane-1,2-diol (12.7 mL, 14.1 g, 227.3 mmol, 3.0 equiv) and p-toluene sulfonic acid monohydrate (0.29 g, 1.52 mmol, 0.02 equiv) in toluene (50 mL) was heated to reflux under Dean-Stark conditions for 1 h. The reaction mixture was extracted with ethyl acetate (3×200 mL), the combined organic phases washed with a sat. solution of sodium carbonate (4×50 mL) and dried over MgSO4. Removal of the solvent by evaporation under reduced pressure yielded 23.3 g (100%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 4.00-4.12 (m, 4H), 5.76 (s, 1H), 7.55-7.56 (m, 2H), 7.65-7.66 (m, 1H). MS (EI): 306.8 [M]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under Dean-Stark conditions for 1 h
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×200 mL)
  4. washthe combined organic phases washed with a sat. solution of sodium carbonate (4×50 mL)
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent
  7. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-d1ec108c6aa84ea795287ebd6367f6a8
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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