Sodium Iodide → 3-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid (acetyloxy)methyl ester

HRID 1492869Notes

Reaction equation

HRID 1492869 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:29]=2[O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:20]=1)[C:15]([OH:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:50]([O:53][CH2:54]Cl)(=[O:52])[CH3:51].[I-].[Na+].C(N(CC)CC)C>CC(C)=O.CN(C=O)C>[C:50]([O:53][CH2:54][O:16][C:15](=[O:17])[C:14]1[CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:29]=2[O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:20]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:13]=1)(=[O:52])[CH3:51]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 69366Chloromethyl acetateHCID 189515713-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid

Product 1

HCID 541636573-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid (acetyloxy)methyl esterYield 23.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g (0.75 mmol) of 3-(decyloxy)-5-[[6-[2,3-bis (phenylmethoxy)phenyl]hexyl]oxy]benzoic acid, 0.25 g (2.25 mmol) of chloromethyl acetate, 0.23 g (1.5 mmol) of sodium iodide and 0.31 ml (2.25 mmol) of triethylamine in 15 ml of acetone and 5 ml of DMF was stirred at reflux under argon for 19 hours. The solvent was removed under reduced pressure, NaHCO3 solution was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to an oil which was purified by HPLC using 10% ethyl acetate-hexane to give 0.13 g of 3-(decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid (acetyloxy)methyl ester as an oil. A mixture of 0.13 g of 3-(decyloxy)-5-[[6-[2,3-bis (phenylmethoxy)phenyl]hexyl]oxy]benzoic acid (acetyloxy)methyl ester and 0.1 g of 10% palladium on carbon in 15 ml of ethyl acetate was stirred under a hydrogen atmosphere for 3.5 hours when uptake ceased. The usual workup gave 0.07 g of 3-(decyloxy)-5-[[6-(2,3-dihydroxyphenyl)hexyl]oxy]benzoic acid (acetyloxy) methyl ester as an oil. The structure was confirmed by the nmr and mass spectra.

Workup

  1. temperatureat reflux under argon for 19 hours
  2. customThe solvent was removed under reduced pressure, NaHCO3 solution
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to an oil which
  7. customwas purified by HPLC

Sources & evidence

ORD record
ord-5842502d5cad441f9f90e9ba3d63375c
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

Loading…