Ethylene Glycol → HCID 86719348, compound

HRID 1519435Notes

Reaction equation

HRID 1519435 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:9]=1)[CH:5]=[O:6].[CH2:15](O)[CH2:16][OH:17]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:17][CH2:16][CH2:15][O:6]2)[CH:7]=[C:8]([O:10][C:11]([F:12])([F:13])[F:14])[CH:9]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 50067113-Bromo-5-(trifluoromethoxy)benzaldehyde

Product 1

HCID 86719348HCID 86719348, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3-bromo-5-trifluoromethoxybenzaldehyde (20, 2.00 g, 7.43 mmol), ethylene glycol (2.31 g, 37.2 mmol), para-toluenesulfonic acid (50 mg, 0.26 mmol) in anhydrous toluene (50 mL) was refluxed using a Dean-Stark apparatus for 3 h. The solution was concentrated and the product purified by silica gel chromatography eluting with 0-10% EtOAc in hexanes to afford the title compound (1.25 g, 54%) as a clear, colorless oil: 1H NMR (500 MHz, CDCl3) δ 7.57 (t, J=1.5 Hz, 1H), 7.37 (s, 1H), 7.28 (s, 1H), 5.79 (s, 1H), 4.12-4.01 (m, 4H).

Workup

  1. customfor 3 h
  2. concentrationThe solution was concentrated
  3. customthe product purified by silica gel chromatography
  4. washeluting with 0-10% EtOAc in hexanes

Sources & evidence

ORD record
ord-11a5f2c7e9e041e1b5428642699b75fc
Source dataset
uspto-grants-2015_07
Patent number
US09073878B2

Reaction notes

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