Benzyl Alcohol → 1-(Phenylmethyl) butanedioate

HRID 1418291Notes

Reaction equation

HRID 1418291 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.Cl>C(N(CC)CC)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

5

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 7922Succinic anhydride

Product 1

HCID 87881-(Phenylmethyl) butanedioateYield 97%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

10 g (100 mmole) of succinic anhydride, 10 mL (97 mmole) of benzyl alcohol and 10 mL of triethylamine were combined, the mixture was heated to reflux, allowed to reflux for about 5 minutes, and then was allowed to stir unheated for 1 hour. After this time, the mixture was poured into 250 mL of 1M hydrochloric acid and was extracted with 2-75 mL portions of ethyl acetate. The organic phases were combined, washed with deionized water, washed with brine, and then were dried over anhydrous magnesium sulfate. The organic phase was concentrated to oil which upon sitting yielded crystalline 19.6 g (94% yield) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureto reflux for about 5 minutes
  4. extractionwas extracted with 2-75 mL portions of ethyl acetate
  5. washwashed with deionized water
  6. washwashed with brine
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. concentrationThe organic phase was concentrated to oil which

Sources & evidence

ORD record
ord-308da10d40b94ca9a419c2a52991a3f6
Source dataset
uspto-grants-1999_03
Patent number
US05883077

Reaction notes

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