Diethyl Ether → 2-(3-Methoxyphenyl)propyl 2-Phenylethyl Ether

HRID 2166640Notes

Reaction equation

HRID 2166640 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)(O)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 20496803HCID 20496803, compound

Product 1

HCID 204969232-(3-Methoxyphenyl)propyl 2-Phenylethyl Ether

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a 0° C. solution of 2-(3-methoxyphenyl)-2-hydroxypropyl 2-phenyl ethyl ether (498 mg., 1.74 mmole) in pyridine (2 ml.) is added dropwise phosphorous oxychloride (477 μl., 5.22 mmole). The reaction is allowed to wa to 20° C. over a 1.5 hour period. It is then stirred for 1.5 hours at 20° C. and then added to ether (150 ml.) and 15% sodium carbonate (100 ml.). The organic phase is separated and washed with 15% sodium carbonate (3×50 ml.), dried over magnesium sulfate and evaporated to an oil. The oil is dissolved in absolute ethanol (15 ml.), 10% palladium-on-carbon (100 mg.) added and the mixture stirred under one atmosphere of hydrogen gas. When hydrogen uptake ceases the reaction is filtered through diatomaceous earth and the filtrate evaporated to an oil. The oil is purified via preparative layer chromatography on silica gel plates, eluted twice with 6:1 pentane:ether to yield the title compound.

Workup

  1. customThe organic phase is separated
  2. washwashed with 15% sodium carbonate (3×50 ml.)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to an oil
  5. dissolutionThe oil is dissolved in absolute ethanol (15 ml.)
  6. addition10% palladium-on-carbon (100 mg.) added
  7. stirringthe mixture stirred under one atmosphere of hydrogen gas
  8. filtrationis filtered through diatomaceous earth
  9. customthe filtrate evaporated to an oil
  10. customThe oil is purified via preparative layer chromatography on silica gel plates
  11. washeluted twice with 6:1 pentane

Sources & evidence

ORD record
ord-c813f12d73674839ac9fbb65ef0d7a92
Source dataset
uspto-grants-1983_06
Patent number
US04387229

Reaction notes

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