Sodium Hydroxide → HCID 19091843, compound

HRID 488290Notes

Reaction equation

HRID 488290 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][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][CH3:28])[CH:7]=[CH:6][C:5]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[OH-].[Na+]>CO>[CH2:11]([O:10][C:8]1[CH:7]=[CH:6][C:5]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[C:4]([CH:9]=1)[C:3]([OH:37])=[O:2])[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][CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54139536HCID 54139536, compound

Product 1

HCID 19091843HCID 19091843, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2.4 g (4.7 mmol) of 5-(octadecyloxy)-2-(phenylmethoxy)benzoic acid methyl ester in 70 ml of methanol and 23 ml (23 mmol) of 1.0N NaOH was stirred at reflux for 4 hours when a clear solution was obtained. The solvent was removed at reduced pressure and the residue was treated with water, acidified to pH 1 with 3N HCl and the product was extracted with chloroform. The dried extract was concentrated to a solid which was recrystallized from ether-hexane to give 2.33 g (99% yield, mp 80°-81°) of 5-(octadecyloxy)-2-(phenylmethoxy)benzoic acid.

Workup

  1. temperatureat reflux for 4 hours when a clear solution
  2. customwas obtained
  3. customThe solvent was removed at reduced pressure
  4. additionthe residue was treated with water
  5. extractionthe product was extracted with chloroform
  6. extractionThe dried extract
  7. concentrationwas concentrated to a solid which
  8. customwas recrystallized from ether-hexane

Sources & evidence

ORD record
ord-f654d547a0424a6988975d38159aa30a
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

Loading…