Benzyl Alcohol → 1-(Phenylmethyl) butanedioate

HRID 507014Notes

Reaction equation

HRID 507014 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.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C(OCC)(=O)C>[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

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 7922Succinic anhydrideHCID 10796Cesium carbonate

Product 1

HCID 87881-(Phenylmethyl) butanedioateYield 70.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5.0 g (0.05 mol) of succinic acid anhydride, 5.4 g (0.05 mol) of benzyl alcohol, 16.25 g (0.05 mol) of cesium carbonate, and 50 ml of N,N-dimethylforamide was stirred at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, and then poured into 200 ml of ethyl acetate. The mixture was washed with saturated aqueous NaCl containing 0.35 N HCl (3×100 mL). The ethyl acetate phase, which contains the product, was collected and dried over anhydrous MgSO4. The MgSO4 was removed via filtration, and the ethyl acetate was removed under reduced pressure. The crude product was purified by crystallization in diethyl ether and hexane to provide 7.34 g of succinic acid monobenzyl ester, 70.47%.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe mixture was washed with saturated aqueous NaCl containing 0.35 N HCl (3×100 mL)
  3. customwas collected
  4. dry with materialdried over anhydrous MgSO4
  5. customThe MgSO4 was removed via filtration
  6. customthe ethyl acetate was removed under reduced pressure
  7. customThe crude product was purified by crystallization in diethyl ether

Sources & evidence

ORD record
ord-f4d393c05f184f7fbd779904b5d5b30f
Source dataset
uspto-grants-2010_08
Patent number
US07786134B2

Reaction notes

Loading…