2-(3-Methoxyphenoxy)acetic acid → 2-(3-Methoxyphenoxy)ethanol

HRID 1511862Notes

Reaction equation

HRID 1511862 reaction equation
B.C1COCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[O:12][CH2:13][C:14](O)=[O:15]>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[O:12][CH2:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 749692-(3-Methoxyphenoxy)acetic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 122988842-(3-Methoxyphenoxy)ethanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250 ml three-necked round-bottomed flask equipped with temperature probe and nitrogen bubbler was charged with 1M Borane/THF solution (60.4 ml, 60.4 m mol) and a solution of (3-Methoxy-phenoxy)-acetic acid (5.00 g, 27.4 mmol) in THF (2.0 ml) was added dropwise, maintaining reaction temperature below 30° C. The reaction was allowed to stir at room temperature overnight. The reaction was quenched by dropwise addition of methanol (20 ml) maintaining the reaction temperature below 35° C. The reaction was stirred at room temperature for 4 hours and concentrated under reduced pressure to yield 2-(3-Methoxy-phenoxy)-ethanol (4.51 g, 98%) as a clear oil which was used without further purification.

Workup

  1. customA 250 ml three-necked round-bottomed flask equipped with temperature probe and nitrogen bubbler
  2. temperaturemaintaining
  3. customreaction temperature below 30° C
  4. customThe reaction was quenched by dropwise addition of methanol (20 ml)
  5. temperaturemaintaining the reaction temperature below 35° C
  6. stirringThe reaction was stirred at room temperature for 4 hours
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7cd89b1b2a0f4266880392ab6139ab3d
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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