Water → HCID 20337466, compound

HRID 1706271Notes

Reaction equation

HRID 1706271 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH:11]([C:13]2[CH:18]=[C:17]([O:19]C)[CH:16]=[CH:15][C:14]=2[O:21]C)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl.N1C=CC=CC=1.O>CCOCC>[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH:11]([C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=2[OH:21])[CH3:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10176127Pyridinium chlorideHCID 20337455HCID 20337455, compound

Product 1

HCID 20337466HCID 20337466, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 2-(2,5-dimethoxyphenyl)propyl 2-phenylethyl ether (195 mg., 0.65 mM), pyridine (0.4 ml., 4.96 mM) and dry pyridine hydrochloride (4 g., 34.6 mM) is heated at 190° C. for 6 hours. The reaction mixture is cooled and added to a mixture of water (100 ml.) and ether (150 ml.). The ether extract is washed once with water (50 ml.) and, along with a second ether extract (50 ml.) of the aqueous phase, is dried over magnesium sulfate and evaporated to dryness. The residue is purified via preparative layer chromatography on silica gel plates by elution with ether-pentane.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionThe ether extract
  3. washis washed once with water (50 ml.) and, along with a second ether
  4. extractionextract (50 ml.) of the aqueous phase
  5. dry with materialis dried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue is purified via preparative layer chromatography on silica gel plates by elution with ether-pentane

Sources & evidence

ORD record
ord-2500306b9fad4558becbba8eec94b3ac
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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