Benzyl Alcohol → HCID 54271345, compound

HRID 2182825Notes

Reaction equation

HRID 2182825 reaction equation
C(C(O)=O)CCCCCCCCCCCCCC(O)=O.C(O)C1C=CC=CC=1.S(=O)(=O)(O)O.[CH2:34]([O:41][C:42]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([O:60]CC1C=CC=CC=1)=[O:59])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(O)(C)C.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH2:34]([O:41][C:42]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 10459Hexadecanedioic acidHCID 684436161,14-Tetradecane dicarboxylic acid dibenzyl ester

Product 1

HCID 54271345HCID 54271345, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

A method of synthesis for a compound obtained by converting one terminal of 1,14-tetradecane dicarboxylic acid into a benzyl ester is described. The compound can be synthesized by using Japanese Patent Application Public Disclosure (Kokai) Hei 04-18245 or “Organic Synthesis II” pages 276-277 as references. That is, 5 g (17.5 millimoles) of 1,14-tetradecane dicarboxylic acid, 8.37 g of benzyl alcohol, 50 ml of toluene and para-toluene sulfonic acid were placed in a flask and were allowed to reflux while using a Dean Stark dehydration device to remove water. After eight hours of refluxing, about one milliliter of water had been removed. The reaction solution was dissolved in hexane and washed using a saturated sodium bicarbonate solution first and water second. The organic phase was dried using sodium sulfate, and the solvent was removed using reduced pressure distillation. The product was recrystallized using hexane, and 8.1 g of 1,14-tetradecane dicarboxylic acid dibenzyl ester was obtained. Next, 4.8 g (16.7 millimoles) of 1,14-tetradecane dicarboxylic acid, 1.8 g of benzyl alcohol, 50 ml of toluene and sulfuric acid were freshly added to 5.97 g (12.8 millimoles) of this 1,14-tetradecane dicarboxylic acid dibenzyl ester, and the mixture was heated and allowed to reflux for five hours. The reaction mixture was subsequently dissolved in 300 ml of isopropanol/chloroform (1/5 volumetric ratio), and the solution was washed with water and dried using sodium sulfate. The solution was concentrated under reduced pressure and recrystallized using a mixed solvent of ether/hexane (1/4 volumetric ratio) to obtain 3.77 g (10.1 millimoles) of 1,14-tetradecane dicarboxylic acid monobenzyl ester.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for five hours
  3. washthe solution was washed with water
  4. customdried
  5. concentrationThe solution was concentrated under reduced pressure
  6. customrecrystallized

Sources & evidence

ORD record
ord-8a68344113d54713a678ca68904596ff
Source dataset
uspto-grants-2005_05
Patent number
US06897326B2

Reaction notes

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