Water → Phenylpropiolic Acid
Reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.BrBr.O>C(O)(=O)C>[C:4]1([C:3]#[C:2][C:1]([OH:11])=[O:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Cinnamic acid (29.6 g) was dissolved in acetic acid (80 ml) under heating and then bromine (32 g) was added dropwise. After stirring at 50° C. for 15 minutes, the resulting mixture was allowed to cool under standing and water (100 ml) was gradually added. The white crystals formed were filtered, washed with water and dried (yield: 56 g). Potassium hydroxide (56 g) was dissolved into methanol (20 ml) and then the above crystals were added in small portions to this solution. The methanol was removed under stirring with heating over a water bath. The residue was dissolved into 200 ml of water and neutralized with a diluted sulfuric acid under ice cooling. Freed pale yellow oil rapidly solidified. The solidified crystals were filtered and recrystallized from water to afford phenylpropiolic acid (22 g).
Workup
- temperatureunder heating
- additionwas gradually added
- customThe white crystals formed
- filtrationwere filtered
- washwashed with water
- customdried (yield: 56 g)
- dissolutionPotassium hydroxide (56 g) was dissolved into methanol (20 ml)
- additionthe above crystals were added in small portions to this solution
- customThe methanol was removed
- stirringunder stirring
- temperaturewith heating over a water bath
- dissolutionThe residue was dissolved into 200 ml of water
- filtrationThe solidified crystals were filtered
- customrecrystallized from water
Sources & evidence
- ORD record
- ord-b85476ed6d5e4c4dacdcbed626ee5c4f
- Source dataset
- uspto-grants-1985_12
- Patent number
- US04560763
Reaction notes
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