Succinic anhydride → Succinic acid Fluorenylmethyl Ester

HRID 861660Notes

Reaction equation

HRID 861660 reaction equation
[C:1]1([CH2:14][OH:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1>ClCl>[C:1]1([CH2:14][O:15][C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydride2×HCID 523071-Fluorenemethanol

Product 1

HCID 69916676Succinic acid Fluorenylmethyl Ester

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

Fluorenemethanol (10.0 g, 51.0 mmol) was dissolved in 150 ml CH2 Cl2, and succinic anhydride (5.6 g, 56 mmol) was added. The solution was stirred for 6 h, and a further portion of succinic anhydride (2.5 g, 25 mmol) was added, and stirring continued overnight. The reaction appeared complete by TLC. The solvent was then removed, and the residue extracted with ethyl acetate, washed with 1% HCl, water, brine, dried (MgSO4) and evaporated to an oil which crystallized on standing. A quantitative yield of crude product was obtained which was used without further purification.

Workup

  1. additionwas added
  2. stirringstirring continued overnight
  3. customThe solvent was then removed
  4. extractionthe residue extracted with ethyl acetate
  5. washwashed with 1% HCl, water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to an oil which
  8. customcrystallized on standing

Sources & evidence

ORD record
ord-5018902a28b049b794e878e2041b1e57
Source dataset
uspto-grants-1998_02
Patent number
US05714606

Reaction notes

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