Hydrochloric Acid → 5-(Benzyloxy)cyclobutabenzen-1(2H)-one

HRID 404320Notes

Reaction equation

HRID 404320 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:16][C:15](OC)([O:17]C)[C:13]=2[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1.O.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:16][C:15](=[O:17])[C:13]=2[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 583801585-(Benzyloxy)-1,1-dimethoxy-1,2-dihydrocyclobutabenzene

Product 1

HCID 583803075-(Benzyloxy)cyclobutabenzen-1(2H)-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

H7.1 (270 mg, 1.00 mmol) was dissolved in 6 mL 5:1 THF and water. To this solution was added 0.5 mL 1N HCl, and the resulting mixture was stirred for 1 hour. The resulting mixture was then diluted with 20 mL EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4, filtered, and concentrated in the presence of silica gel. The residue was then purified by column chromatography with 10% EtOAc/hexane to afford H7.2 (204 mg, yield, 91.1%). MS ESI (pos.) m/e: 225.1 (M+H)+.

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in the presence of silica gel
  5. customThe residue was then purified by column chromatography with 10% EtOAc/hexane
  6. customto afford
  7. customH7.2 (204 mg, yield, 91.1%)

Sources & evidence

ORD record
ord-edccee1f97fc49749382e3781619ed4d
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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