Diethyl Ether → 3-(3',4'-Dimethoxyphenyl)-1-propanol

HRID 641852Notes

Reaction equation

HRID 641852 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13](O)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl-].[NH4+].C(OCC)C>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 750193-(3,4-Dimethoxyphenyl)propionic acid

Product 1

HCID 775283-(3',4'-Dimethoxyphenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.0 g (28.5 mmol) 3-(3,4-dimethoxyphenyl)-propionic acid in 120 ml anhydrous THF is cooled to 0° C. and treated within 15 minutes with 42.75 ml borane THF complex (1 M solution). Stirring is continued overnight at rt. The resulting clear solution is cooled with an ice/water bath and hydrolyzed by the addition of 100 ml saturated ammonium chloride solution. Extractive work-up with diethyl ether furnishes a colourless oil, which is purified by chromatography (hexane/ethyl acetate) to yield a colourless oil.

Workup

  1. additiontreated within 15 minutes with 42.75 ml borane THF complex (1 M solution)
  2. customis purified by chromatography (hexane/ethyl acetate)
  3. customto yield a colourless oil

Sources & evidence

ORD record
ord-ee140966544442e2944a477051e243a8
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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