Water → 4-(Octadecyloxy)-alpha-oxobenzeneacetic acid

HRID 488294Notes

Reaction equation

HRID 488294 reaction equation
C([O:3][C:4](=[O:32])[C:5](=[O:31])[C:6]1[CH:11]=[CH:10][C:9]([O:12][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][CH2:29][CH3:30])=[CH:8][CH:7]=1)C.[OH-].[Na+].O>CO>[CH2:13]([O:12][C:9]1[CH:8]=[CH:7][C:6]([C:5](=[O:31])[C:4]([OH:32])=[O:3])=[CH:11][CH:10]=1)[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][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 539208914-(Octadecyloxy)-alpha-oxobenzeneacetic acid ethyl ester

Product 1

HCID 190918534-(Octadecyloxy)-alpha-oxobenzeneacetic acidYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.9 g (6.45 mmol) of 4-(octadecyloxy)-alpha-oxobenzeneacetic acid ethyl ester in 200 ml of hot methanol was added 7.1 ml (7.1 mmol) of 1.0 N NaOH. The reaction mixture was stirred at reflux for 5 minutes, 50 ml of water was added and the solvents were removed at reduced pressure. Water (300 ml) was added and the product was extracted with methylene chloride-THF (4:1). The dried extract was concentrated at reduced pressure and the residual solid was recrystallized from acetone-hexane to give 2.39 g (88% yield, mp 78°-80°) of 4-(octadecyloxy)-alpha-oxobenzeneacetic acid.

Workup

  1. temperatureat reflux for 5 minutes
  2. customthe solvents were removed at reduced pressure
  3. additionWater (300 ml) was added
  4. extractionthe product was extracted with methylene chloride-THF (4:1)
  5. extractionThe dried extract
  6. concentrationwas concentrated at reduced pressure
  7. customthe residual solid was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-ee70d8a7936a4d9985956d7867971cc6
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

Loading…