Hydrochloric Acid → HCID 136348822, compound

Temperature

0 °C

In a 250 ml round bottom flask equipped with a magnetic stirrer was added 7.60 g (61.7 mmol) p-anisidine, 26 ml conc. HCl(aq), 150 ml absolute ethanol, and 150 ml deionized water. Sodium nitrite (4.58 g, 66.3 mmol) in 30 ml water was added dropwise over 30 minutes while keeping the reaction mixture at −10° C. The reaction mixture was stirred for an additional 1 hour. 300 mg sulfamic acid was added and the mixture was stirred for an additional 20 minutes. The solids were filtered out and the cold diazonium solution was set aside. (5-chloro-2-hydroxy-1,3-phenylene)dimethanol from Example 3 was dissolved in 100 ml deionized water. Approximately one-fourth by volume of a solution comprised of 12.7 g (318 mmol) NaOH in water was added to the (5-chloro-2-hydroxy-1,3-phenylene)dimethanol solution and the reaction mixture was cooled to 0° C. The diazonium mixture and remaining NaOH solution were added simultaneously to the (5-chloro-2-hydroxy-1,3-phenylene)dimethanol mixture over 30-60 minutes. The reaction mixture was stirred at room temperature for 16 hours. The mixture was poured into 3 L deionized water and acidified to pH 4 with 1 N HCl. The solid was filtered and washed with several liters water and vacuum dried at 50° C. to afford a dark solid.

1. customIn a 250 ml round bottom flask equipped with a magnetic stirrer
2. customat −10° C
3. stirringthe mixture was stirred for an additional 20 minutes
4. filtrationThe solids were filtered out
5. dissolution(5-chloro-2-hydroxy-1,3-phenylene)dimethanol from Example 3 was dissolved in 100 ml
6. stirringThe reaction mixture was stirred at room temperature for 16 hours
7. additionThe mixture was poured into 3 L
8. filtrationThe solid was filtered
9. washwashed with several liters water and vacuum
10. customdried at 50° C.
11. customto afford a dark solid

ORD record

ord-a4d4533a5d22444f8388d7f9fc3dbfbb

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207244B2