Benzyl Alcohol → 1-(Phenylmethyl) butanedioate

HRID 989929Notes

Reaction equation

HRID 989929 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:8]([O:15][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 311Citric AcidHCID 1049PyridineHCID 7922Succinic anhydride

Product 1

HCID 87881-(Phenylmethyl) butanedioate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Succinic anhydride (30 g, 300 mmole) was dissolved in methylene chloride (300 ml). To the solution were added benzyl alcohol (10.2 ml, 100 mmole), 4-dimethylaminopyridine (1.22 g, 10 mmole) and pyridine (48 ml). After 3 hours the reaction mixture was poured in to citric acid aqueous solution. The organic phase was concentrated to small volume and sodium hydrogen carbonate and water were added. Then mixture was stirred for 30 min. The aqueous phase was collected, and to it was added citric acid aqueous solution. The product precipitated out, was collected and mixed 15.3 g.

Workup

  1. concentrationThe organic phase was concentrated to small volume and sodium hydrogen carbonate and water
  2. additionwere added
  3. customThe aqueous phase was collected
  4. additionto it was added citric acid aqueous solution
  5. customThe product precipitated out
  6. customwas collected
  7. additionmixed 15.3 g

Sources & evidence

ORD record
ord-d6fe42060dd4400f8f9041cd034e8aea
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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