Water → 3-Phenoxy-benzeneethanol

HRID 384130Notes

Reaction equation

HRID 384130 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][C:15](O)=[O:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>O1CCCC1.B.O1CCCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 1417493-Phenoxyphenylacetic acid

Product 1

HCID 139291293-Phenoxy-benzeneethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2723981Borane;tetrahydrofuranSolvent

Procedure

To a solution of (3-phenoxyphenyl)acetic acid (1.157 g) in tetrahydrofuran (23 ml), 6.5 ml of borane-tetrahydrofuran complex (1.17M tetrahydrofuran solution) was added, and the reaction solution was stirred at room temperature for 2 hours. To the reaction solution was added water, and the mixture was extracted with chloroform 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: ethyl acetate/hexane (10:90-80/20)) to afford the title compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (10:90-80/20))

Sources & evidence

ORD record
ord-41d8072ff54f4585ac33d72cb7cc8a8f
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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