Water → 2-(2-Phenoxyphenyl)ethanol

HRID 384144Notes

Reaction equation

HRID 384144 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C([BH3-])#N.[Na+].[O:21]1CCC[CH2:22]1>ICI.C[Li]>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][CH2:22][OH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 88060o-PhenoxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 198491432-(2-Phenoxyphenyl)ethanol

Reagents, catalysts & solvents 2

HCID 6346DiiodomethaneSolventHCID 178418348HCID 178418348, compoundSolvent

Procedure

To a solution of 2-phenoxybenzaldehyde (535 mg) in tetrahydrofuran (5 ml), 0.326 ml of diiodomethane and 5.4 ml of methyllithium (1.0M diethyl ether solution) were added under ice-cooling, and the reaction solution was stirred at the same temperature for 30 minutes and then at room temperature for 1 hour. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in tetrahydrofuran (5 ml), 284 mg of sodium cyanoborohydride and 0.569 ml of trifluoroborane-diethyl ether complex were added under ice-cooling, and the reaction solution was stirred at the same temperature for 50 minutes. To the reaction solution was added a saturated saline solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50/50)) to afford the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. waitat room temperature for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto afford a crude product as a yellow oil
  8. temperaturecooling
  9. stirringthe reaction solution was stirred at the same temperature for 50 minutes
  10. additionTo the reaction solution was added a saturated saline solution
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe combined organic layers were washed with a saturated saline solution
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationThe solvent was distilled off under reduced pressure
  15. customthe residue obtained
  16. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50/50))

Sources & evidence

ORD record
ord-51b92cf373b441cab84b850b9e07ca68
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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