Acetic Acid → HCID 86586555, compound

HRID 1582509Notes

Reaction equation

HRID 1582509 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]2

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6547AzobisisobutyronitrileHCID 8028Tetrahydrofuran2×HCID 8058Hexane

Product 1

HCID 86586555HCID 86586555, compound

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 three hours. The viscous reaction mass was cooled to room temperature and diluted with 10.5 ml of THF. The solution was poured dropwise into 85 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 67.3%. The polymer obtained was an alternating polymer. The weight average molecular weight was found to be 7987 g/mole with polydispersity of 2.92. 1H NMR indicated the presence of both methyl and t-butyl ester of MCA and BNC respectively. The monomer ratio in the polymer was found to be 53:47 (MCA:BNC).

Workup

  1. customTo a 35 ml pressure tube equipped with a Teflon coated stir bar
  2. customscrew cap
  3. customThe vessel was placed in an oil-bath
  4. customwas preheated to 72° C
  5. waitto proceed for three hours
  6. filtrationThe white polymer was filtered
  7. washwashed with hexane
  8. customdried overnight in a vacuum oven at 55° C
  9. customThe polymer obtained

Sources & evidence

ORD record
ord-3ebd7603d7474137b4f9065337b72df8
Source dataset
uspto-grants-2004_05
Patent number
US06737215B2

Reaction notes

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