5-Chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid methyl ester → 5-Chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid

HRID 1613059Notes

Reaction equation

HRID 1613059 reaction equation
C[O:2][C:3](=[O:44])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19]=2[O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:6]([CH2:40][CH2:41][CH3:42])[C:5]=1[OH:43]>CO.O1CCOCC1.[OH-].[Na+]>[Cl:10][C:8]1[C:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:19]=2[O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:6]([CH2:40][CH2:41][CH3:42])[C:5]([OH:43])=[C:4]([CH:9]=1)[C:3]([OH:44])=[O:2]

Participants

5

Reactant 1

HCID 149863355-Chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid methyl ester

Product 1

HCID 149863365-Chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acidYield 71.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.30 g of 5-chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid methyl ester in 10 mL of methanol, 5 mL of dioxane and 2.5 mL of 1N sodium hydroxide was left at room temperature for 3 days. The solvent was removed under reduced pressure and the residue was acidified and extracted with ethyl acetate. The dried extract was concentrated and chromatographed on 30 g of silica gel using acetic acid: ethyl acetate: toluene (1:25:75) to give 0.21 g of 5-chloro-2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid as an oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. extractionThe dried extract
  4. concentrationwas concentrated
  5. customchromatographed on 30 g of silica gel

Sources & evidence

ORD record
ord-32b0b9bb4f65420083d6f9e558076cb4
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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