Phenol → HCID 21957500, compound

HRID 2213574Notes

Reaction equation

HRID 2213574 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH2:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:23]=[O:24])(=O)=O>CN(C)C=O>[O:7]([CH2:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:23]=[O:24])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 21957468[2-(Benzyloxy)-5-formylphenyl]methyl methanesulfonate

Product 1

HCID 21957500HCID 21957500, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenol (100 mg), cesium carbonate (100 mg) and 3-[[(methylsulfonyl)oxy]methyl]-4-phenylmethoxybenzaldehyde (120 mg) were heated in dimethylformamide (1 ml) at approx. 80° C. for about 30 minutes. TLC showed that the reaction was almost complete so the reaction mixture was partitioned between diethyl ether and water. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give an oil. The residue was purified via flash column chromatography, using dichloromethane:diethyl ether (10:1) as eluant to give 3-[(phenoxy)methyl]-4-phenylmethoxybenzaldehyde (90 mg) as off-white crystals. 1H NMR (CDCl3) δ 9.95 (s, 1H, CHO); 5.27 (s, 2H); 5.24 (s, 2H). TLC (silica gel): Rf=0.7 (petroleum ether: diethyl ether, 1:1).

Workup

  1. customwas partitioned between diethyl ether and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. customThe residue was purified via flash column chromatography

Sources & evidence

ORD record
ord-19c0eada5c6546dd8efb9546c5b94fbc
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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