m-Phenylenediacetic acid → 2-[3-(2-Hydroxyethyl)phenyl]ethanol

HRID 1297074Notes

Reaction equation

HRID 1297074 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12](O)=[O:13])[CH:8]=[CH:9][CH:10]=1)(O)=[O:2].CSC.B>C1COCC1>[OH:2][CH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][OH:13])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 29788m-Phenylenediacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 100807412-[3-(2-Hydroxyethyl)phenyl]ethanolYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3-carboxymethylphenyl)acetic acid (1.0 g, 5.15 mmol) in THF (100 mL) was added slowly borane dimethyl sulfide (2.3 mL, 30.9 mmol). The resulting solution was stirred overnight (˜18 hours) and then quenched by slowly adding 1N HCl (100 mL). The mixture was then extracted using EtOAc (3×100 mL) and the combined organic layers were washed with saturated NaCl (100 mL), dried over magnesium sulfate, filtered and concentrated under vacuum to provide 750 mg of the title intermediate (87% yield), which was used without further purification.

Workup

  1. customquenched
  2. additionby slowly adding 1N HCl (100 mL)
  3. extractionThe mixture was then extracted
  4. washthe combined organic layers were washed with saturated NaCl (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c19bed6d430147f0bfef639057c6ffaa
Source dataset
uspto-grants-2007_07
Patent number
US07250414B2

Reaction notes

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