Toluene → HCID 18921242, compound

HRID 2364592Notes

Reaction equation

HRID 2364592 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[CH2:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 8221Stearyl AlcoholHCID 140984-Vinylbenzoic acid

Product 1

HCID 18921242HCID 18921242, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 2.91 g (20 mmol) of 4-vinylbenzoic acid, 5.84 g (22 mmol) of 1-octadecanol, 0.17 g (1 mmol) of 4-toluenesulfonic acid, and 75 ml of toluene was heated at reflux with water separated azeotropically using a Dean-Stark trap. After 16 hours, the mixture was cooled to ambient temperature and filtered through a short column of basic alumina, eluting with tetrahydrofuran. The filtrate was concentrated to deposit a solid product, which was purified by chromatography on silica gel (a heptane/dichloromethane eluate), followed by recrystallization from acetonitrile. A white solid was obtained, mass 3.98 g (51% yield).

Workup

  1. temperaturewas heated
  2. customseparated azeotropically
  3. filtrationfiltered through a short column of basic alumina
  4. washeluting with tetrahydrofuran
  5. concentrationThe filtrate was concentrated
  6. customwas purified by chromatography on silica gel (a heptane/dichloromethane eluate),
  7. customfollowed by recrystallization from acetonitrile
  8. customA white solid was obtained

Sources & evidence

ORD record
ord-ad04ed577d5d40fab59da7a2b7226a2d
Source dataset
uspto-grants-2014_04
Patent number
US08692238B2

Reaction notes

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