Hydrochloric Acid → Phenol, 2,2′-[oxybis(2,1-ethanediyloxy)]bis[4-amino-

HRID 988065Notes

Reaction equation

S(O)(=O)([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=O.[N:12]([O-])=O.[Na+].Cl.[OH:17][C:18]1[CH:37]=[CH:36][CH:35]=[CH:34][C:19]=1[O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26]C1C=CC=CC=1O.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-:46].[Na+]>O>[OH:46][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][C:19]1[CH:34]=[C:35]([NH2:12])[CH:36]=[CH:37][C:18]=1[OH:17]

Participants

Conditions

Temperature: 2.5 °C

Procedure

In a 600 ml glass beaker, 13.9 g (0.08 mole) of sulfanilic acid were dissolved in 41 ml of 10% sodium hydroxide solution and a solution of 5.7 g (0.08 mole) of sodium nitrite in 30 ml of water was added to the resulting solution. After the mixture had been cooled to 0-5° C., 72 ml of 10% hydrochloric acid were added dropwise over a period of 45 minutes. This cold diazonium solution was then added dropwise over a period of 30 minutes at 0-5° C. to a solution of 11.8 g (0.04 mole) of bis-([-2-(2-hydroxyphenoxy)-ethyl]-ether (prepared in accordance with J. Am. Chem. Soc. (1977), 2568) in 66 ml of 10% sodium hydroxide. After stirring for another 1.5 hours at 15° C., 38.3 g (0.22 mole) of sodium dithionite were added. The mixture was then heated for 20 minutes to 75° C., the product precipitating. After cooling, the product was filtered off under suction, washed with water and dried in vacuo at 70° C. The product had a melting point of 215° C. (with decomposition).

Workup

temperatureThe mixture was then heated for 20 minutes to 75° C.
customthe product precipitating
temperatureAfter cooling
filtrationthe product was filtered off under suction
washwashed with water
customdried in vacuo at 70° C

Sources & evidence

ORD record: ord-3b4437a799ef4b7eaac6263627b539de
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06635241B1

Reaction notes

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