Terephthalaldehyde → 4-Cyanostilbene-4'-aldehyde
Reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[OH-].[K+].C(OP([CH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1)(OCC)=O)C>CO>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([CH:21]=[CH:6][C:5]2[CH:8]=[CH:9][C:2]([CH:1]=[O:10])=[CH:3][CH:4]=2)=[CH:23][CH:24]=1)#[N:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
With stirring, cooling and blanketing with nitrogen, 6.7 g of terephthalaldehyde are added in portions to a mixture of 6.2 ml of aqueous potassium hydroxide solution 50% w/v and 40 ml of methanol, such that the temperature does not exceed 22° C. The resultant solution is then treated dropwise at 10° C. over 1/2 hour with a solution of 12.7 g of p-diethylphosphonomethylbenzonitrile (99.5%) in 10 ml of methanol, whereupon the reaction product soon precipitates. After stirring overnight at 10° C., the thick suspension is neutralised with 3 ml of glacial acetic acid, diluted with 40 ml of water, and filtered with suction. The filter residue is washed repeatedly with a 3:2 mixture of methanol/water and then with water until salt-free and dried under vacuum at 80° C., affording 10.6 g of 4-cyanostilbene-4'-aldehyde as a pale yellow powder.
Workup
- temperaturecooling
- customdoes not exceed 22° C
- customsoon precipitates
- stirringAfter stirring overnight at 10° C.
- additiondiluted with 40 ml of water
- filtrationfiltered with suction
- washThe filter residue is washed repeatedly with a 3:2 mixture of methanol/water
- dry with materialwith water until salt-free and dried under vacuum at 80° C.
Sources & evidence
- ORD record
- ord-440b588564de4ffba647310ad7ef0456
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04778622
Reaction notes
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