Dimethylformamide → HCID 66988705, compound

HRID 1753664Notes

Reaction equation

HRID 1753664 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].CN(C=[O:19])C.C(N(CC)CC)C.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29]>O.C(OC)(C)(C)C>[C:9]([OH:14])(=[O:19])[CH:10]=[CH2:11].[C:27]([OH:30])(=[O:1])[CH:28]=[CH2:29].[CH:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:3]1[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 13140Acryloyl chloride2×HCID 15731(1,1'-Biphenyl)-2,2'-diol

Product 1

HCID 66988705HCID 66988705, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a 1000 ml 3 neck round bottom equipped with an overhead stirrer and temperature probe was added 2,2′-dihydroxy-biphenyl (50 g), Prostab 5198 (0.02 g), DMF (150 ml) and triethylamine (59.8 g). The reaction was cooled to <0 C with methanol/dry ice bath and acryloyl chloride (51 g) was slowly added. The GC indicated the reaction was mostly complete with ˜15% monoacrylate. Triethylamine (10 g) was added followed by the addition of acryloyl chloride (9 g). The GC indicated the reaction was complete. The reaction product was treated with (300 ml) methyl t-butyl ether and (300 ml) DI water. The organic portion was separated and washed 5 times with 200 ml sodium chloride brine. The organic portion was treated with 50 g filter aid, mixed and filtered through a thin pad of silica gel. The filtrate was concentrated in vacuo to recover a yellow oil. This oil (69 g) was taken up in 300 ml chloroform and filtered through a short silica gel column (5.5 inch diameter by 4 inches thick) and eluted with chloroform/heptane. The product (52 g) was recovered by concentrating the eluent in vacuo. GC indicated >98% product. The refractive index of the (i.e. uncured) monomer was determined to be 1.571.

Workup

  1. temperatureThe reaction was cooled to <0 C with methanol/dry ice bath
  2. customThe organic portion was separated
  3. washwashed 5 times with 200 ml sodium chloride brine
  4. additionThe organic portion was treated with 50 g
  5. filtrationfilter aid
  6. additionmixed
  7. filtrationfiltered through a thin pad of silica gel
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto recover a yellow oil
  10. filtrationfiltered through a short silica gel column (5.5 inch diameter by 4 inches thick)
  11. washeluted with chloroform/heptane
  12. customThe product (52 g) was recovered
  13. concentrationby concentrating the eluent in vacuo

Sources & evidence

ORD record
ord-c204d73f656e4a488336284fb852ac20
Source dataset
uspto-grants-2015_10
Patent number
US09164195B2

Reaction notes

Loading…