Quinone → HCID 18681482, compound

HRID 1699647Notes

Reaction equation

HRID 1699647 reaction equation
[C:1](OCC1C=CC(N(C)C)=CC=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(Cl)(=O)C(C)=C.[CH3:23][N:24]([CH3:34])[C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30][OH:31])=[CH:27][CH:26]=1.C(N(CC)CC)C.C1(=O)C=CC(=O)C=C1>C1C=CC=CC=1>[C:1]([O:31][CH2:30][CH2:29][C:28]1[CH:32]=[CH:33][C:25]([N:24]([CH3:23])[CH3:34])=[CH:26][CH:27]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 5

HCID 4650QuinoneHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 93252p-N,N-DimethylaminophenethanolHCID 18681488HCID 18681488, compound

Product 1

HCID 18681482HCID 18681482, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

This monomer was synthesized in a manner analogous to the published method used for the synthesis of 4-(dimethylamino)benzyl methacrylate. Thus, 4.55 g (0.0435 mol) methacryloyl chloride in 4.55 g benzene was added dropwise to a solution of 5.0 g (0.03 mol) 4-dimethylaminophenethyl alcohol, 3.64 g (0.036 mol) triethylamine, and 8.7 g benzene in the presence of p-benzoquinone and CuCl(I) with stirring and cooling, keeping the temperature below 15° C. The reaction mixture was left to stir for one hour in a room temperature water bath (about 25° C.). The solution was filtered to remove triethylamine hydrochloride. The benzene filtrate was washed with water and then with saturated sodium carbonate solution, dried over sodium sulfate anhydrous, filtered, and the benzene removed with the rotary evaporator (water bath 20-25° C.). The monomer was distilled in vacuo in the presence of CuCl(I) and 2,2-diphenyl-1-picrylhydrazyl (DPPH), bp=115-122° C./95-100, μHg. The monomer was recrystallized from petroleum ether, mp=42-43° C. The analysis for nitrogen showed 5.86% N (calc. 6.00). NMR δ(ppm): 1.9 (s, 3, CH2═C(CH3)—); 2.8 (m, 2, —CH2—CH2—C6H4—); 2.9 (s, 6, CH3)2); 4.2-4.3 (m, 2, —(O)C—O—CCH2—CH2—); 5.5, 6.1 (d, s, 2, CH2═C); 6.7, 7.1 (d, d, 4, aromitic H).

Workup

  1. customThis monomer was synthesized in a manner analogous to the published method
  2. temperaturecooling
  3. customthe temperature below 15° C
  4. waitThe reaction mixture was left
  5. stirringto stir for one hour in a room temperature water bath (about 25° C.)
  6. filtrationThe solution was filtered
  7. customto remove triethylamine hydrochloride
  8. washThe benzene filtrate was washed with water
  9. dry with materialwith saturated sodium carbonate solution, dried over sodium sulfate anhydrous
  10. filtrationfiltered
  11. customthe benzene removed with the rotary evaporator (water bath 20-25° C.)
  12. distillationThe monomer was distilled in vacuo in the presence of CuCl(I) and 2,2-diphenyl-1-picrylhydrazyl (DPPH), bp=115-122° C./95-100, μHg
  13. customThe monomer was recrystallized from petroleum ether, mp=42-43° C

Sources & evidence

ORD record
ord-c8c40abe4c594a50945330283bd9616b
Source dataset
uspto-grants-2002_02
Patent number
US06348429B1

Reaction notes

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