Sulfuric Acid → alpha-Hydroxyacetophenone
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:11].BrBr.C([O-])=O.[Na+].C(OC)(=O)NN>CO.O.O.CO>[OH:11][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]Participants
Conditions
- Temperature
- 20 °C
Procedure
A 100-gallon glass lined kettle equipped with a cooling jacket was charged with 90.5 lbs. of acetophenone, 123 lbs. of methanol and 340 mls. of 98% sulfuric acid. The reactor was cooled to 20° C and the mixture was stirred during the addition of 119 lbs. of bromine that was added incrementally by a gravity fed system at a rate so that the temperature was maintained at between 20°-25° C over a 3-hour period. After the bromination was complete, 37 lbs. of methanol, 240 lbs of water and 112 lbs. of sodium formate were added. The mixture was stirred with agitation overnight at 60° C and after cooling to 40° C a solution of 68 lbs. methyl carbazate in 45 lbs. of a 54:46 methanol-water mixture was added. The reaction mixture was stirred for 2-hours at 40° C to form the carbomethoxy nydrazone of α-hydroxy acetophenone. Thereafter the reaction mixture was allowed to cool to 20° C, was centrifuged, and washed with water on the centrifuge.
Workup
- customequipped with a cooling jacket
- additionwas charged with 90.5 lbs
- temperaturewas maintained at between 20°-25° C over a 3-hour period
- stirringThe mixture was stirred with agitation overnight at 60° C
- temperatureafter cooling to 40° C a solution of 68 lbs
- stirringThe reaction mixture was stirred for 2-hours at 40° C
Sources & evidence
- ORD record
- ord-3c777ec6682f484f8377f2cc7d343f6f
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04105848
Reaction notes
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