p-Phenylenediacetic acid → 1,4-Benzenediethanol

HRID 1297079Notes

Reaction equation

HRID 1297079 reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](O)=[O:13])=[CH:7][CH:6]=1)(O)=[O:2].CSC.B>C1COCC1>[OH:2][CH2:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 81760p-Phenylenediacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 50132051,4-BenzenediethanolYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4-carboxymethylphenyl)acetic acid (1.0 g, 5.15 mmol) in THF (100 mL) was slowly added borane dimethyl sulfide (2.3 mL, 30.9 mmol) and the resulting mixture was stirred overnight (˜18 hours). The reaction was then quenched by slowly adding 1N HCl (100 mL). The resulting mixture was then extracted with EtOAc (3×100 mL). The combined organic layers were washed with saturated NaCl (1×100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to provide 750 mg of the title intermediate (87% yield), which was used without further purification.

Workup

  1. customThe reaction was then quenched
  2. additionby slowly adding 1N HCl (100 mL)
  3. extractionThe resulting mixture was then extracted with EtOAc (3×100 mL)
  4. washThe combined organic layers were washed with saturated NaCl (1×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5a260b9e4fbe4612a89f6a25aeddfba7
Source dataset
uspto-grants-2007_07
Patent number
US07250414B2

Reaction notes

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