Benzyl Alcohol → 1-(Phenylmethyl) butanedioate

HRID 1682081Notes

Reaction equation

HRID 1682081 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH2:11][CH2:10]1.CCN(CC)CC>C1COCC1>[CH2:1]([O:8][C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 7922Succinic anhydrideHCID 8471Triethylamine

Product 1

HCID 87881-(Phenylmethyl) butanedioateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.13 mL (4.32 g, 40 mmol) of benzyl alcohol and 4.40 g (44 mmol) of succinic anhydride in 100 mL of THF at 0° C. was added at once 12.24 mL (8.90 g, 88 mmol) of Et3N. The mixture was allowed to come to room temperature and stirred for 18 h at which time it was concentrated under vacuum to a viscous oil and partitioned between 100 mL of 1 N HCl and 100 mL of EtOAc. The EtOAc layer was extracted with 84 mL of 5% NaHCO3 solution. The aqueous layer was acidified with concentrated HCl solution to pH 1 and extracted with two 50 mL portions of EtOAc. The EtOAc layers were combined and washed with brine, dried (MgSO4), filtered, and concentrated to give 6.9 g (83%) of 21 as a white chunky solid: 1H NMR (CDCl3) 2.70 (s, 4H), 5.22 (s, 2H), 7.38 (s, 5H).

Workup

  1. customto come to room temperature
  2. concentrationwas concentrated under vacuum to a viscous oil
  3. custompartitioned between 100 mL of 1 N HCl and 100 mL of EtOAc
  4. extractionThe EtOAc layer was extracted with 84 mL of 5% NaHCO3 solution
  5. extractionextracted with two 50 mL portions of EtOAc
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e90b6b3b2039445fbb407ed1dfeb7fc4
Source dataset
uspto-grants-1992_12
Patent number
US05175257

Reaction notes

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