Benzyl Alcohol → HCID 561730, compound

HRID 2416956Notes

Reaction equation

HRID 2416956 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:1]1([C:5]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chloride

Product 1

HCID 561730HCID 561730, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Cyclobutanecarbonyl chloride (2.37 g, 20 mmols) was added to a chloroform (30 ml) solution of benzyl alcohol (2.16 g, 20 mmols) and triethylamine (2.2 g, 22 mmols) with cooling with ice, and then heated under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and extracted with ether. The organic layer was washed with 1 N HCl, an aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate and the solvent was evaporated. The resulting oil was purified through silica gel column chromatography (developer:hexane/acetone=10/1) and distilled (110° C./1.2 mmHg) to obtain 2.14 g (yield: 56%) of benzyl cyclobutanecarboxylate as a colorless oil.

Workup

  1. temperaturewith cooling with ice
  2. temperatureheated
  3. temperatureunder reflux for 1 hour
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionthe residue was diluted with water
  6. extractionextracted with ether
  7. washThe organic layer was washed with 1 N HCl
  8. dry with materialan aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate
  9. customthe solvent was evaporated
  10. customThe resulting oil was purified through silica gel column chromatography (developer:hexane/acetone=10/1)
  11. distillationdistilled (110° C./1.2 mmHg)

Sources & evidence

ORD record
ord-e477274fb9924e8d9d4cb79a13be2e7d
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

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