Water → HCID 86691493, compound

HRID 1482772Notes

Reaction equation

HRID 1482772 reaction equation
[CH:1]1[C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.N1C=CC=CC=1.ClC(Cl)([O:20][C:21](=[O:27])[O:22]C(Cl)(Cl)Cl)Cl.O>C(Cl)Cl>[CH:1]1[C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[C:21](=[O:20])([O-:27])[O-:22]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10393TyrosolHCID 94429Triphosgene

Product 1

HCID 86691493HCID 86691493, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 500 mL 3-necked round-bottomed flask equipped with a mechanical stirrer, and a liquid addition device were placed 10 g (0.073 mol) of tyrosol, 24 ml (0.298 mol) of pyridine, 200 mL of DCM and stirred for 15 min to get a clear solution. Triphosgene (7.7 g, 0.078 mol of phosgene) was dissolved in 25 mL of DCM and the solution was introduced into the reaction flask over 2-3 hours. After the addition was complete, 250 mL of water was added to the reaction mixture and stirred for 5 min. After allowing the layers to separate, the top aqueous layer was removed and discarded. The washing was repeated with two additional 250 mL portions of DI water. The reaction mixture was then precipita-ted with 300 mL of IPA. The resulting gel was ground twice with 200 mL portions of IPA in 1 L laboratory blender. The product was isolated by vacuum filtration and dried in a vacuum oven at 60° C. The polymer had a HPSEC polystyrene equivalent molecular weight of 126 Kda (THF as mobile phase) and glass transition temperature (Tg) of 58° C. Compression molding at 195° C. gave a uniform transparent film which gave tensile modulus, tensile stress at yield, and elongation at break respectively of 19.1 ksi, 5 ksi and 450%.

Workup

  1. customIn a 500 mL 3-necked round-bottomed flask equipped with a mechanical stirrer
  2. additiona liquid addition device
  3. customto get a clear solution
  4. additionthe solution was introduced into the reaction flask over 2-3 hours
  5. additionAfter the addition
  6. stirringstirred for 5 min
  7. customto separate
  8. customthe top aqueous layer was removed
  9. customThe product was isolated by vacuum filtration
  10. customdried in a vacuum oven at 60° C
  11. customa HPSEC polystyrene equivalent molecular weight of 126 Kda (THF as mobile phase) and glass transition temperature (Tg) of 58° C
  12. customCompression molding at 195° C. gave a uniform transparent film which
  13. customgave tensile modulus, tensile stress
  14. customat yield

Sources & evidence

ORD record
ord-06dbaceaffc54c3da05e6ca8be653ac0
Source dataset
uspto-grants-2016_08
Patent number
US09416090B2

Reaction notes

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