Sodium Hydroxide → 3-(Octadecyloxy)-5-(phenylmethoxy)benzoic acid

HRID 488268Notes

Reaction equation

HRID 488268 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([O: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][CH2:35][CH3:36])[CH:5]=1.[OH-].[Na+]>CO.O1CCOCC1>[CH2:19]([O:18][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=1)[C:3]([OH:37])=[O:2])[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][CH2:35][CH3:36]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 540335133-(Octadecyloxy)-5-(phenylmethoxy)benzoic acid methyl ester

Product 1

HCID 193890463-(Octadecyloxy)-5-(phenylmethoxy)benzoic acidYield 88.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3.0 g (7.1 mmol) of 3-hydroxy-5-(octadecyloxy) benzoic acid methyl ester, 0.93 ml (7.85 mmol) of benzyl bromide and 2.0 g (14.5 mmol) of potassium carbonate in 50 ml of DMF was stirred at 85° for 50 hours. The solvent was removed at reduced pressure and the residue was extracted with methylene chloride. The extract was concentrated and recrystallized from methylene chloride-methanol to give 3.24 g (89% yield, mp 62°-64°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid methyl ester. A solution of 3.24 g (6.3 mmol) of 3-(octadecyloxy)-5-(phenylmethoxy) benzoic acid methyl ester and 3 ml (18 mmol) of 6N NaOH in 100 ml of methanol and 25 ml of dioxane was stirred at reflux for 3.5 hours. The solvents were removed at reduced pressure and the residue was acidified and extracted with ethyl acetate. The dried extract was concentrated to a solid which was recrystallized from methylene chloride-hexane to give 2.77 g (88% yield, mp 101°-103°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid.

Workup

  1. temperatureat reflux for 3.5 hours
  2. customThe solvents were removed at reduced pressure
  3. extractionextracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated to a solid which
  6. customwas recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-efbc7d945bff479d813f1ddb0ef6639e
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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