Sodium Hydroxide → HCID 19091767, compound

HRID 488298Notes

Reaction equation

HRID 488298 reaction equation
C[O:2][C:3](=[O:31])[C:4](=[O:30])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][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][CH3:29])[CH:6]=1.[OH-].[Na+]>CO>[CH2:12]([O:11][C:7]1[CH:6]=[C:5]([C:4](=[O:30])[C:3]([OH:31])=[O:2])[CH:10]=[CH:9][CH:8]=1)[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]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54044136HCID 54044136, compound

Product 1

HCID 19091767HCID 19091767, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.98 g (6.9 mmol) of 3-(octadecyloxy)-alpha-oxobenzeneacetic acid methyl ester in 200 ml of hot methanol was added 7.6 ml (7.6 mmol) of 1N NaOH. The solution was stirred at reflux for 5 minutes and the solvent was then removed under reduced pressure. The residue was treated with water and 15 ml of 1N HCl and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was recrystallized form acetone-hexane to give 2.5 g (88% yield, mp 77°-79°) of 3-(octadecyloxy)-alpha-oxobenzeneacetic acid.

Workup

  1. temperatureat reflux for 5 minutes
  2. customthe solvent was then removed under reduced pressure
  3. additionThe residue was treated with water and 15 ml of 1N HCl
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas recrystallized
  8. customform acetone-hexane

Sources & evidence

ORD record
ord-89faa48ba07b4d7badf960b20e16a256
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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