p-Toluenesulfonic acid monohydrate → 3-((Benzyloxy)methyl)cyclobutanone

HRID 1241503Notes

Reaction equation

HRID 1241503 reaction equation
C[O:2][C:3]1(OC)[CH2:6][CH:5]([CH2:7][O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[CH2:9]([O:8][CH2:7][CH:5]1[CH2:6][C:3](=[O:2])[CH2:4]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21934943{[(3,3-Dimethoxycyclobutyl)methoxy]methyl}benzene

Product 1

HCID 118198503-((Benzyloxy)methyl)cyclobutanoneYield 58%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a stirring solution of [(3,3-dimethoxy-cyclobutyl)methoxymethyl]-benzene (13.0 g, 55.1 mmol) in 200 mL of a mixture of acetone:water (3:1) was added p-toluenesulfonic acid mono hydrate (2.1 g, 11.0 mmol). The reaction mixture was heated to 65 C for 45 minutes. Both TLC and GS/MS analysis indicated complete consumption of starting material. The reaction was cooled to room temperature and then the acetone was removed under reduced pressure. The resulting mixture was diluted with ethyl acetate and washed with an aqueous solution 5% NaOH. The layers were separated and the organic layer was dried over magnesium sulfate, filtered through a fritted funnel and then concentrated under reduced pressure. Purification of this material was accomplished by flash chromatography using a Biotage Column 75 small, eluting with a 10% EtOAc/hexanes. The product containing fractions were collected and concentrated under reduced pressure to yield the title compound (6.0 g, 58% yield) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was heated to 65 C for 45 minutes
  2. customconsumption of starting material
  3. customthe acetone was removed under reduced pressure
  4. additionThe resulting mixture was diluted with ethyl acetate
  5. washwashed with an aqueous solution 5% NaOH
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. filtrationfiltered through a fritted funnel
  9. concentrationconcentrated under reduced pressure
  10. customPurification of this material
  11. washeluting with a 10% EtOAc/hexanes
  12. additionThe product containing fractions
  13. customwere collected
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48768e7338cd4c228e14e7cc107ed7d9
Source dataset
uspto-grants-2006_10
Patent number
US07115600B2

Reaction notes

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