Acetic Acid → 4-(Octadecyloxy)-alpha-oxobenzeneacetic acid ethyl ester

HRID 488293Notes

Reaction equation

HRID 488293 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:16])[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH3:4].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C(O)(=O)C>CN(C=O)C>[CH2:3]([O:5][C:6](=[O:16])[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])=[CH:10][CH:9]=1)[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 82181-BromooctadecaneHCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetate

Product 1

HCID 539208914-(Octadecyloxy)-alpha-oxobenzeneacetic acid ethyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 0.325 g (8.1 mmol) of a 60% oil dispersion of NaH suspended in 15 ml of anhydrous DMF and stirred under an argon atmosphere at room temperature was added 1.5 g (7.73 mmol) of 4-hydroxyalpha-oxobenzeneacetic acid ethyl ester. The reaction mixture was stirred at room temperature for 20 minutes and a solution of 3.2 g (9.66 mmol) of 1-bromooctadecane in 20 ml of anhydrous DMF was added dropwise over 15 minutes. After stirring at reflux for 16 hours, 5 ml of acetic acid was added and the solvent was removed at reduced pressure. Water was added to the residue and the product was extracted with methylene chloride. The dried extract was concentrated at reduced pressure and the solid residue was purified by HPLC using 50% methylene chloride-hexane to give 2.9 g (84% yield, mp 46°-48°) of 4-(octadecyloxy)-alpha-oxobenzeneacetic acid ethyl ester.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 minutes
  2. stirringAfter stirring
  3. temperatureat reflux for 16 hours
  4. customthe solvent was removed at reduced pressure
  5. additionWater was added to the residue
  6. extractionthe product was extracted with methylene chloride
  7. extractionThe dried extract
  8. concentrationwas concentrated at reduced pressure
  9. customthe solid residue was purified by HPLC

Sources & evidence

ORD record
ord-b9d2762b01b74e42975597cf7c85dcd8
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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