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 Na2 SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=207 (M−OH+CH3 CN).

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. customdried over Na2 SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-dc0c1eccece546a2a7c5d4790321fd2b

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071772B2