Water → 1-{5'-[2-(3,4-Bis(hydroxymethyl)phenyl)ethyl]-2'-methyl-2-propylbiphenyl-4-yl}propan-1-one

HRID 584319Notes

Reaction equation

HRID 584319 reaction equation
[CH2:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[C:25]([CH2:31][OH:32])[CH:24]=4)[CH:15]=3)=[C:10]([CH2:33][CH2:34][CH3:35])[CH:9]=2)OCC[O:4]1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O>[OH:32][CH2:31][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C:16]2[CH:17]=[CH:18][C:19]([CH3:20])=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:3](=[O:4])[CH2:1][CH3:2])=[CH:9][C:10]=3[CH2:33][CH2:34][CH3:35])[CH:15]=2)[CH:28]=[CH:27][C:26]=1[CH2:29][OH:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 22345598HCID 22345598, compound

Product 1

HCID 223455891-{5'-[2-(3,4-Bis(hydroxymethyl)phenyl)ethyl]-2'-methyl-2-propylbiphenyl-4-yl}propan-1-oneYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

640 mg (1.4 mmol) of (4-{2-[4′-(2-ethyl[1,3]dioxolan-2-yl)-6-methyl-2′-propylbiphenyl-3-yl]ethyl}-2-hydroxymethylphenyl)methanol are placed in 15 ml of acetone and 15 ml of water in a round-bottomed flask. A spatula-tip of p-toluenesulfonic acid is added and the solution is refluxed for 2 hours 30 minutes. At room temperature, it is poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (30/70). 300 mg (50%) of the expected product are obtained in the form of a colorless oil.

Workup

  1. temperaturethe solution is refluxed for 2 hours 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (30/70)

Sources & evidence

ORD record
ord-5b6caba6a0f54ddb9cb5a1b54f77e7af
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

Loading…