Water → HCID 22610268, compound

HRID 2306776Notes

Reaction equation

HRID 2306776 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)(O)[CH2:6][CH2:5]2)[O:3]C1.O>C(O)(C(F)(F)F)=O>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:7]2[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH:6]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 962WaterHCID 152326818-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 22610268HCID 22610268, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 4-(4-Fluoro-phenyl)-4-hydroxy-cyclohexanone ethylene ketal (8.23 g, 32.6 mmol) from Step 1 was stirred in TFA (25 mL) for 15 minutes. The reaction mixture was poured into H2O (100 mL) and then extracted with CHCl3 (2×75 mL). The organic solution was washed with saturated bicarbonate, dried (Na2SO4), filtered and concentrated under reduced pressure to afford crude 1-(4-fluorophenyl)-cyclohexen-4-one (6.44 g): 1H NMR (300 MHz, CDCl3) δ 7.35 (dd, J=8, 8 Hz, 2H), 7.04 (dd, J=8, 8 Hz, 2H), 6.05 (m, 1H), 3.05 (m, 2H), 2.87 (m, 2H), 2.65 (dd, J=7, 7 Hz, 2H).

Workup

  1. extractionextracted with CHCl3 (2×75 mL)
  2. washThe organic solution was washed with saturated bicarbonate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69accf8a44794bdc9d755f8ca0420cf6
Source dataset
uspto-grants-2004_12
Patent number
US06828341B2

Reaction notes

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