p-Toluenesulfonic acid → 6-(9H-Carbazol-9-yl)hexyl prop-2-enoate

HRID 1876630Notes

Reaction equation

HRID 1876630 reaction equation
[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[C:32](O)(=[O:35])[CH:33]=[CH2:34].COC1C=CC(O)=CC=1>C1(C)C=CC=CC=1>[CH:10]1[C:11]2[N:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:32](=[O:35])[CH:33]=[CH2:34])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 90154-MethoxyphenolHCID 6402679H-carbazole-9-hexanol

Product 1

HCID 576231746-(9H-Carbazol-9-yl)hexyl prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 500 ml three-neck round bottom flask was added 33 g. of 6-carbazol-9-yl-hexan-1-ol, 170 g. toluene, 2.2 g. PTSA, 10.7 g. acrylic acid and 0.07 g. hydroquinone monomethyl ether (MEHQ). The mixture was heated to reflux and the water was removed by azeotropic distillation using a Dean-Stark trap. After five hours of reflux, 1 gram additional acrylic acid was added and the mixture heated for one additional hour. The reaction mixture was cooled to room temperature, washed with 100 g 5% HCl in water, then 100 g. 10% sodium carbonate in water, then 100 g. of saturated brine. The solvent was removed on a rotary evaporator.

Workup

  1. additionTo a 500 ml three-neck round bottom flask was added 33 g
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. customthe water was removed by azeotropic distillation
  5. temperatureAfter five hours of reflux
  6. addition1 gram additional acrylic acid was added
  7. temperaturethe mixture heated for one additional hour
  8. washwashed with 100 g 5% HCl in water
  9. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-aefebafb9f39412094f4765cc7842085
Source dataset
uspto-grants-2012_11
Patent number
US08309650B2

Reaction notes

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