Benzyl Alcohol → HCID 1653334, compound

HRID 2421802Notes

Reaction equation

HRID 2421802 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.CN(C1C=CC=CN=1)C.[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C[C:26]([O:29]C)(C)C>>[CH2:26]([O:29][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 7922Succinic anhydrideHCID 15413tert-Butyl methyl etherHCID 218852-Dimethylaminopyridine

Product 1

HCID 1653334HCID 1653334, compound

Conditions

Temperature
68 °C

Procedure

In a 500 mL round bottom flask, fitted with a reflux, condenser, succinic anhydride (10.03 g, 1.2 eq.) and dimethylaminopyridine (10.2 g, 1 eq.) and benzyl alcohol (9.01 g, 1 eq.) in MTBE (250 mL) were combined. The reaction mixture was placed under inert atmosphere and stirred in an oil bath at 68° C. for 4 hours. The reaction was then quenched with a solution of 10% NaHCO3 and extracted with MTBE. The organic layer was washed with NaHCO3 and brine. The organic layer was collected, dried using MgSO4, and concentrated to give a white solid. The crude product was purified using column chromatography to give 14.1 g of white crystals.

Workup

  1. customThe reaction was then quenched with a solution of 10% NaHCO3
  2. extractionextracted with MTBE
  3. washThe organic layer was washed with NaHCO3 and brine
  4. customThe organic layer was collected
  5. customdried
  6. concentrationconcentrated
  7. customto give a white solid
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-765a239e316a442e83596c6ca62eee75
Source dataset
uspto-grants-2011_06
Patent number
US07959958B2

Reaction notes

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