Succinic anhydride → Succinic acid mono-(2,4,6-trimethylbenzyl) ester

HRID 507016Notes

Reaction equation

HRID 507016 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH2:4][OH:5].[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH2:4][O:5][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 10796Cesium carbonateHCID 201392,4,6-Trimethylbenzyl alcohol

Product 1

HCID 68466934Succinic acid mono-(2,4,6-trimethylbenzyl) esterYield 46.62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.50 g (0.01 mol) of 2,4,6-trimethylbenzyl alcohol, 1.00 g (0.01 mol) of succinic acid anhydride, 3.25 g (0.01 mol) of cesium carbonate, and 100 ml of dioxane was stirred at reflux temperature for 4 hours. The reaction mixture was cooled to room temperature and then filtered to remove the solid cesium carbonate. The solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (acetone-hexane) to provide 1.167 g of succinic acid mono-(2,4,6-trimethylbenzyl) ester (46.62%).

Workup

  1. temperatureat reflux temperature for 4 hours
  2. filtrationfiltered
  3. customto remove the solid cesium carbonate
  4. customThe solvent was removed under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (acetone-hexane)

Sources & evidence

ORD record
ord-1fca4d2884b84a3f92b7a2dda51079a3
Source dataset
uspto-grants-2010_08
Patent number
US07786134B2

Reaction notes

Loading…