Sodium Iodide → 1-(4-(2-(3,5-Bis(hydroxymethyl)phenoxy)ethoxy)phenyl)ethanone

HRID 2405720Notes

Reaction equation

HRID 2405720 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Br[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[CH:26][CH:25]=1>CC(N(C)C)=O>[OH:9][CH2:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=1)[O:1][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 15194153,5-Di(hydroxymethyl)phenolHCID 234408111-(4-(2-Bromoethoxy)phenyl)ethanone

Product 1

HCID 594401711-(4-(2-(3,5-Bis(hydroxymethyl)phenoxy)ethoxy)phenyl)ethanoneYield 86%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of (5-hydroxy-1,3-phenylene)dimethanol (3.0, 20.0 mmol), sodium carbonate (2.5 g, 29.0 mmol) and sodium iodide (0.45 g, 2.9 mmol) in 60 ml of DMA was added 1-(4-(2-bromoethoxy)phenyl)ethanone (5.0, 20.57 mmol). The mixture was stirred overnight, evaporated and purified on SiO2 chromatography eluted with EtAc/Hexane (4:1 to 5:1) to afford 5.41 g (86%) of the title compound. 1H NMR (CD3OD) 7.99 (ddd, 2H, J=2.8, 4.8, 9.8 Hz), 7.07 (ddd, 2H, J=2.8, 4.7, 9.8 Hz), 6.94 (s, 1H), 6.89 (s, 2H), 4.58 (s, 4H), 4.42 (dd, 2H, J=2.2, 6.1 Hz), 4.37 (m, 2H), 2.55 (s, 3H); 13C NMR 199.55, 164.66, 160.59, 144.72, 132.03, 131.74, 119.16, 115.64, 113.11, 68.36, 67.87, 65.20, 26.53; MS m/z+ 339.2 (M+Na).

Workup

  1. customevaporated
  2. custompurified on SiO2 chromatography
  3. washeluted with EtAc/Hexane (4:1 to 5:1)

Sources & evidence

ORD record
ord-eee3b84e4996450995f28e145f1ae357
Source dataset
uspto-grants-2014_08
Patent number
US08809320B2

Reaction notes

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