Succinic anhydride → HCID 68464609, compound

HRID 507015Notes

Reaction equation

HRID 507015 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 10796Cesium carbonateHCID 115054-Methylbenzyl alcohol

Product 1

HCID 68464609HCID 68464609, compoundYield 90.58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.44 g (0.02 mol) of 4-methylbenzyl alcohol, 2.00 g (0.02 mol) of succinic acid anhydride, 6.50 g (0.02 mol) of cesium carbonate, and 150 mL of dioxane was stirred at reflux temperature for 4 hours. The mixture was cooled to room temperature and filtered to remove the solid portion. The solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (ethyl acetate-hexane) to provide 4.022 g of succinic acid mono-(4-methylbenzyl) ester (90.58%).

Workup

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

Sources & evidence

ORD record
ord-0017d4e9154b48f7aedfddb0074124f7
Source dataset
uspto-grants-2010_08
Patent number
US07786134B2

Reaction notes

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