Sulfuric Acid → HCID 72739086, compound
Reaction equation
CO[CH:3](OC)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][CH2:15][CH3:16])=[C:8]([CH3:17])[C:7]=1[CH3:18].S(O)(O)(=O)=O.[NH2:26][OH:27].S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:18][C:7]1[C:8]([CH3:17])=[C:9]([CH2:12][CH2:13][O:14][CH2:15][CH3:16])[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][CH:3]=[N:26][OH:27]Participants
Procedure
A mixture of 2.1 liters of methanolic solution of 760 g of 1-(2,2-dimethoxyethoxy)-4-(2-ethoxyethyl)-2,3-dimethylbenzene and 2.1 liters of aqueous solution of 466 g of hydroxylamine sulfate was heated to 70 C. To the mixture added was 12 N sulfuric acid until the pH became 0.5, and the mixture was stirred vigorously. Since the pH is lowers with the progress of the reaction, an aqueous 12 N sodium hydroxide solution was added dropwise so as to maintain pH at 0.5. The reaction was monitored by HPLC, and when the conversion exceeded 95%, the reaction mixture was cooled to around room temperature. Generally, the reaction requires about 10 hours. After pH was adjusted to 6.5 with 12 N-NaOH, the solid formed was filtered. The filtered product was washed with 1.0 liter of warm water, and dried under reduced pressure to obtain the title product. m.p. 102°-105° C., amount obtained 676 g, purity 93%, yield 93%.
Workup
- temperaturewas heated to 70 C
- additionTo the mixture added
- customwith the progress of the reaction
- temperatureto maintain
- temperaturethe reaction mixture was cooled to around room temperature
- customthe solid formed
- filtrationwas filtered
- washThe filtered product was washed with 1.0 liter of warm water
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-75ee0ddb5f5f44efac741c850b5645d5
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04985596
Reaction notes
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