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

4-Nitrophthalic acid (40 g, 189.5 mmol) in tetrahydrofuran (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 was allowed to warm slowly to ambient temperature and stirred for 18 h. Methanol (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 sodium hydroxide 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 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 sodium hydroxide 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

ORD record

ord-2ed271d9ab054db588502b52710d4a63

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696192B2