p-Phenylenediacetic acid → 1,4-Benzenediethanol

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.

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

ORD record

ord-ff07448c96744b35901f2273d18fb697

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557126B2