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

A solution of 4-nitrophthalic acid (40.0 g, 189.5 mmol) in THF (500 mL) was added drop wise over 1.5 h to a solution of borane-THF complex (1 M, 490 mL, 490 mmol), maintaining 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. 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 to give the title compound. MS: m/z=207 (M-OH+CH3CN).

1. temperaturemaintaining the 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

ORD record

ord-dea19415348d44c8a3c74dfa92a209e0

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659300B2