Acetic Acid → HCID 86586555, compound
Reaction equation
[CH3:1][C:2](N=N[C:8]([C:11]#N)([CH3:10])[CH3:9])([C:4]#[N:5])[CH3:3].[C:13]([OH:16])(=[O:15])[CH3:14].C[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH2:23]1C[O:26]CC1>>[C:4]([C:2](=[CH2:3])[C:1]([O:15][CH3:13])=[O:26])#[N:5].[C:14]12([C:13]([O:16][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:15])[CH2:23][CH:20]([CH2:19][CH2:18]1)[CH:21]=[CH:22]2Participants
Procedure
To a 35 ml pressure tube equipped with a Teflon coated stir bar and a threaded Teflon cap with O-ring was added MCA (1.46 g, 13.1 mmol), BNC (5.08 g, 26.2 mmol), THF (4 g), AIBN (120 mg) and acetic acid (200 mg). The reaction mixture was deaerated with nitrogen at a flow rate of 30 ml/min for 15 minutes. The reaction vessel was then immediately capped tight using the Teflon screw cap. The vessel was placed in an oil-bath, which was preheated to 72° C. The reaction was allowed to proceed for six hours. The viscous reaction mass was cooled to room temperature and diluted with 10.5 ml of THF. The solution was poured dropwise into 125 ml of hexane while stirring. The white polymer was filtered, washed with hexane and dried overnight in a vacuum oven at 55° C. The yield of the isolated polymer was found to be 80.6%. The weight average molecular weight was found to be 7613 with polydispersity of 3.97. 1H NMR indicated the presence of both methyl ((δ1.53) and t-butyl (δ3.95) ester of MCA and BNC respectively. The monomer ratio in the polymer was found to be 52:48 (MCA:BNC).
Workup
- customTo a 35 ml pressure tube equipped with a Teflon coated stir bar
- customscrew cap
- customThe vessel was placed in an oil-bath
- customwas preheated to 72° C
- waitto proceed for six hours
- filtrationThe white polymer was filtered
- washwashed with hexane
- customdried overnight in a vacuum oven at 55° C
Sources & evidence
- ORD record
- ord-a0cc47360ee24d9ab78f6e973151b9fb
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06686429B2
Reaction notes
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