Acetic Acid → HCID 86586555, compound

HRID 2119735Notes

Reaction equation

HRID 2119735 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 8028Tetrahydrofuran3×HCID 8058Hexane

Product 1

HCID 86586555HCID 86586555, compoundYield 64.6%

Procedure

To a 35 (milliliter) 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 (2.54 g, 13.1 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 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 20.5 ml of THF. The solution was poured dropwise into 75 ml of hexane while stirring. The white polymer was filtered, washed with hexane and dried overnight in a vacuum oven at 55° C. The isolated polymer had a yield of 64.6%. The polymer contained blocks of methyl cyanoacrylate. This block configuration yields acidic methylene groups in the backbone which can be utilized favorably. The molecular weight of the copolymer was determined using GPC technique (THF, polystyrene standards) and found to be Mw=5612, Mn, =2349 and PD=2.39. The presence of both methyl ester and t-butyl ester containing monomers was verified by proton NMR (δ1.52, methyl and δ3.94, t-butyl). From the integration of these two peaks, the polymer was found to be contain 64% MCA and 36% BNC. The Tg of the polymer was measured using Differential Scanning Calorimeter (DSC) (TA Instruments, Model 2920) and found to be 137° C.

Workup

  1. customTo a 35 (milliliter) 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. customThis block configuration yields acidic methylene groups in the backbone which
  10. customto be 137° C.

Sources & evidence

ORD record
ord-347c481f321c4fcb8879f298b0a4fc18
Source dataset
uspto-grants-2004_02
Patent number
US06686429B2

Reaction notes

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