HCID 86746125, compound → HCID 86746124, compound

HRID 1885470Notes

Reaction equation

HRID 1885470 reaction equation
[P:1](=[O:53])([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])([O:45][CH3:46])[O:2][CH:3]([CH2:22][O:23]C(C1C=CC(OC)=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CO.C(Cl)(Cl)Cl>[P:1](=[O:53])([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])([O:45][CH3:46])[O:2][CH:3]([CH2:22][OH:23])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 1

HCID 86746125HCID 86746125, compound

Product 1

HCID 86746124HCID 86746124, compoundYield 152%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 10 g of phosphoric acid, 2-(hexadecyloxy)-1-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]ethyl methyl pentyl ester in 100 ml of methyl alcohol and 50 ml of chloroform is brought to a boil, the heat removed and 5 g of Amberlite®-15 resin carefully added. The reaction is stirred at ambient temperature for 2 hours, filtered to remove the resin and the cake washed well with 2:1 methyl alcohol:chloroform. The solvent is removed to give 9.7 g of a thick syrup. The product is chromatographed using dry column silica gel with 1:1 ethyl acetate:hexanes. Product fractions are combined and the solvents evaporated to give 1.38 g of a less polar isomer oily product and 1.46 g of a more polar isomer oily product.

Workup

  1. customthe heat removed
  2. addition5 g of Amberlite®-15 resin carefully added
  3. filtrationfiltered
  4. customto remove the resin
  5. washthe cake washed well with 2:1 methyl alcohol
  6. customThe solvent is removed

Sources & evidence

ORD record
ord-078a8a803ac64a05a511b3563e512f86
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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