Methanol → (4-Nitro-1,2-phenylene)dimethanol

A solution of 4-nitrophthalic acid (40 g, 189.5 mmol) in THF (500 mL) was added dropwise over 1.5 h to a solution of borane-THF complex (1 M, 490 mL, 490 mmol), keeping the reaction temperature between 0° C. and 5° C. After the addition, the reaction mixture was allowed to warm slowly to ambient temperature and stirred for 18 h. MeOH (100 mL) was added carefully and the precipitated solid dissolved. The mixture was concentrated in vacuo to about 500 mL, cooled to 0° C., and 10 N NaOH was added to adjust the pH to 10-11. This mixture was extracted with EtOAc (3×600 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=207 (M−OH+CH3CN).

1. customthe reaction temperature between 0° C. and 5° C
2. additionAfter the addition
3. dissolutionthe precipitated solid dissolved
4. concentrationThe mixture was concentrated in vacuo to about 500 mL
5. temperaturecooled to 0° C.
6. addition10 N NaOH was added
7. extractionThis mixture was extracted with EtOAc (3×600 mL)
8. washthe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD-Eintrag

ord-a22aa8ebe6094a94917e5c64b22d9c71

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08372859B2