Benzyl Alcohol → HCID 22756278, compound

HRID 927205Notes

Reaction equation

HRID 927205 reaction equation
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.[CH2:8](O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:8]([O:6][C:3]1[CH2:4][CH2:5][C:1](=[O:7])[CH:2]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 774661,3-Cyclopentanedione

Product 1

HCID 22756278HCID 22756278, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of cyclopentane-1,3-dione (2.00 g, 20.4 mmol), benzyl alcohol (2.11 mL, 20.4 mmoL) and para-toluenesulfonic acid (35 mg, 0.20 mmol) in toluene (10.0 mL) is heated at reflux over night. Water is added, and the mixture is extracted with dichloromethane. The organic layer is concentrated, and the residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 9:1 to cyclohexane/ethyl acetate 1:4). Yield: 1.66 g; ESI mass spectrum: [M+H]+=189; Retention time HPLC: 0.51 min (X012_S01).

Workup

  1. temperatureis heated
  2. temperatureat reflux over night
  3. extractionthe mixture is extracted with dichloromethane
  4. concentrationThe organic layer is concentrated
  5. customthe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 9:1 to cyclohexane/ethyl acetate 1:4)
  6. custom0.51 min (X012_S01)

Sources & evidence

ORD record
ord-b65c9cac054740fbbf1c437a05171a94
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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