Hydrochloric Acid → 4-Amino-2,6-dimethylphenol
Reaction equation
S(O)(=O)(C1C=CC([NH2:9])=CC=1)=O.C(=O)([O-])[O-].[Na+].[Na+].N([O-])=O.[Na+].Cl.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[OH:31].[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:23][C:24]1[CH:29]=[C:28]([NH2:9])[CH:27]=[C:26]([CH3:30])[C:25]=1[OH:31]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
Sulphanilic acid (43.3 g, 0.25 mol) and sodium carbonate (13.25 g, 0.125 mol) were dissolved in water (250 ml) and cooled to 15° C. Sodium nitrite (18.63 g, 0.27 mol) in water (100 ml) was added in one portion, and the mixture added immediately to concentrated hydrochloric acid (53 ml) and ice (300 g), with stirring. After 30 minutes, the resulting suspension was added to an ice-cold solution of 2,6-dimethylphenol (30.54 g, 0.25 mol) and sodium hydroxide (55 g) in water (550 ml), stirring vigorously. After 2 hours, the temperature was raised to 50°, and sodium dithionite (115 g, 0.66 mol) added portionwise. On heating to 75° the red colour discharged, and after a further 10 minutes, the solution was cooled to room temperature. The resulting white solid was filtered, washed and dried to give the title compound (27.33 g), m.p. 135°-7°.
Workup
- stirringstirring vigorously
- waitAfter 2 hours
- temperaturethe temperature was raised to 50°
- temperatureOn heating to 75° the red colour
- waitafter a further 10 minutes
- temperaturethe solution was cooled to room temperature
- filtrationThe resulting white solid was filtered
- washwashed
- customdried
Sources & evidence
- ORD record
- ord-d073d6f663b1419fbd0d6f7ecf4370f1
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05143920
Reaction notes
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