Borane;tetrahydrofuran → N-Dodecyl-4-ethoxyaniline

N-dodecanoyl-p-ethoxyaminobenzene (6g, 0.019 mole) was placed in a 250 ml round-bottom flask with Borane/THF complex (50 ml, 1M solution in tetrahydrofuran, stabilized with 5 mole percent sodium borohydride). The flask was flushed with nitrogen, stoppered with a drierite tube and allowed to stand at room temperature for 20 hours. Water was then added slowly to react with excess diborane. Formation of the amine salt was avoided by refluxing the reaction mixture with triethylamine (5 ml) for one hour. The mixture was cooled and the layers separated. The upper layer was washed with water (3 × 20 ml). A fourth wash emulsified the mixture. It was broken by addition of salt. The upper layer was dried with anh. sodium sulphate and evaporated to dryness yielding 5.56g (97%) of white plates of crude product. Crystallization from methanol afforded 4.3g (75%) of N-dodecyl-p-ethoxy-aminobenzene in the form of white plates, m.p. 38°-39° C.

1. customThe flask was flushed with nitrogen
2. customstoppered with a drierite tube
3. additionWater was then added slowly
4. customto react with excess diborane
5. temperatureThe mixture was cooled
6. customthe layers separated
7. washThe upper layer was washed with water (3 × 20 ml)
8. washA fourth wash
9. additionIt was broken by addition of salt
10. dry with materialThe upper layer was dried with anh. sodium sulphate
11. customevaporated to dryness
12. customyielding 5.56g (97%) of white plates of crude product
13. customCrystallization from methanol

ORD record

ord-2b50086c7e2a4fefb260e95c82370b9f

Source dataset

uspto-grants-1978_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04076849