Benzyl Alcohol → 1-(Phenylmethyl) butanedioate

HRID 1016619Notes

Reaction equation

HRID 1016619 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12]1>C1COCC1.O>[CH2:1]([O:8][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 7922Succinic anhydrideHCID 24758Sodium hydride

Product 1

HCID 87881-(Phenylmethyl) butanedioateYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl alcohol (0.52 mL, 5 mmol) in THF (20 mL) was treated with NaH (60%, 0.2 g, 5 mmol) and succinic anhydride (0.502 g, 5 mmol) and refluxed for 4 h. After cooling to room temperature, the reaction mixture was diluted with H2O and extracted with EtOAc several times. The combined organic layer was washed H2O and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel using EtOAc:Hex (1:1) as eluant to give 20 as white solid (0.866 g, 57%).

Workup

  1. temperaturerefluxed for 4 h
  2. extractionextracted with EtOAc several times
  3. washThe combined organic layer was washed H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-65b6697c633d42ddaf707eeb810377f2
Source dataset
uspto-grants-2002_11
Patent number
US06476076B1

Reaction notes

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