Water → HCID 20496827, compound

HRID 26091Notes

Reaction equation

HRID 26091 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=2)[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]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10176127Pyridinium chlorideHCID 204969232-(3-Methoxyphenyl)propyl 2-Phenylethyl Ether

Product 1

HCID 20496827HCID 20496827, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 2-(3-methoxyphenyl)propyl 2-phenylethyl ether (176 mg., 0.65 mmole), pyridine (0.4 ml., 4.96 mmole) and dry pyridine hydrochloride (4 g., 34.6 mmole) 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 an oil. The oil is purified via preparative layer chromatography on silica gel plates, eluted six times with 30% ether-pentane to yield the title product.

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 an oil
  7. customThe oil is purified via preparative layer chromatography on silica gel plates
  8. washeluted six times with 30% ether-pentane

Sources & evidence

ORD record
ord-9c65962197f3492cbc1b8e0c23d51280
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

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