Succinic anhydride → Succinic acid Fluorenylmethyl Ester

HRID 634991

Reaction equation

HRID 634991 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>C(Cl)Cl>[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 6344DichloromethaneSolvent

Procedure

Fluorenemethanol (10.0 g, 51.0 mmol) was dissolved in 150 ml CH2Cl2, 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. stirringstirring continued overnight
  2. customThe solvent was then removed
  3. extractionthe residue extracted with ethyl acetate
  4. washwashed with 1% HCl, water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to an oil which
  7. customcrystallized on standing

Sources & evidence

ORD record
ord-64843d96446146ccb080137976478364
Source dataset
uspto-grants-2001_02
Patent number
US06184389B2

Linked notes

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