Water → 1-[2-Hydroxy-4-(4-iodo-benzyloxy)-3-propyl-phenyl]-ethanone

HRID 2267045Notes

Reaction equation

HRID 2267045 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=1.[OH:10][C:11]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(C)=O>[OH:10][C:11]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]([O:20][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=2)[CH:14]=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 9542584-Iodobenzyl bromideHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 574383871-[2-Hydroxy-4-(4-iodo-benzyloxy)-3-propyl-phenyl]-ethanoneYield 52.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add 1-bromomethyl-4-iodo-benzene (10.00 g, 33.7 mmol) to a solution of 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (6.54 g, 33.7 mmol) and cesium carbonate (13.2 g, 40.4 mmol) in acetone (500 mL) and stir. After 48 hours, pour the reaction into water and extract with ethyl acetate. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with a gradient of ethyl acetate:hexanes to yield the title product as a yellow solid (7.20 g, 52%): 1H NMR (CDCl3) δ 0.95 (t, 3H), 1.56 (sextet, 2H), 2.56 (s, 3H), 2.69 (t, 2H), 5.09 (s, 2H), 6.43 (d, 1H), 7.15 (d, 2H), 7.57 (d, 1H), 7.73 (d, 2H), 12.74 (s, 1H).

Workup

  1. additionpour
  2. extractionextract with ethyl acetate
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give a residue
  7. customPurify the residue by flash chromatography
  8. washeluting with a gradient of ethyl acetate

Sources & evidence

ORD record
ord-d46ab30d409941c2903bd92245114c77
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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