Hydrochloric Acid → 4-[(4-Fluorophenyl)methyl]-cyclohexanone

HRID 397164Notes

Reaction equation

HRID 397164 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]2[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 121339518-[(4-Fluorophenyl)methyl]-1,4-dioxaspiro[4.5]decane

Product 1

HCID 121339524-[(4-Fluorophenyl)methyl]-cyclohexanoneYield 64.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 8-[(4-fluorophenyl)methyl]-1,4-dioxaspiro[4.5]decane (18 g, 72 mmol) in 100 mL of THF was added 1 M hydrogen chloride in water (70 mL) followed by conc hydrogen chloride (50 mL). The reaction was heated to reflux for 5 h and then cooled to room temperature. The reaction was conc in vacuo to 120 mL and then extracted with ethyl acetate (3×100 mL). The organic layers were combined, washed with sat sodium bicarbonate, brine, dried over sodium sulfate, and conc in vacuo to a colorless oil. The oil was purified by flash chromatography (SiO2, 10:1 hexanes:ethyl acetate) to yield 9.6 g of a colorless oil. MS (ESI) 207 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 h
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washwashed with sat sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. customThe oil was purified by flash chromatography (SiO2, 10:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-fa11ea672889400ea381b4c86f44664f
Source dataset
uspto-grants-2003_08
Patent number
US06608227B1

Reaction notes

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