2-(4-Fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-epoxycyclohexane → 2-(4-Fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexanone

HRID 6519Notes

Reaction equation

HRID 6519 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[O:18][CH:9]2[C:10]([CH3:17])([CH3:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13]3)=[CH:4][C:3]=1[CH3:19]>C1C=CC=CC=1.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][C:10]([CH3:17])([CH3:16])[C:9]2=[O:18])=[CH:4][C:3]=1[CH3:19]

Participants

4

Reactant 1

HCID 539343032-(4-Fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-epoxycyclohexane

Product 1

HCID 197938982-(4-Fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexanoneYield 80%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a cooled solution (0° C.) of the epoxide from Example 1, Step A above (32.7 g, 125 mmol) in benzene (200 ml) is added dropwise 7.6 ml BF3 ·OEt2 (62 mmol). The cooling bath is removed and the reaction mixture warmed to room temperature and stirred for 2 hours. The benzene is removed under reduced pressure and provides a residue which is dissolved in ether (300 ml) and washed with saturated ammonium chloride. The ether layer is concentrated under reduced pressure to provide 26 g (80%) of 2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexanone. The ketone is recrystallized from pentane to give a white solid; m.p. 63°-64° C.: 1H NMR δ=1.05 (s,3), 1.1 (s,3), 1.3 (s,3), 1.32 (s,3), 1.75 (s,2), 2.0 (q,2), 2.3 (s,3), 3.95 (dd,1), 6.95 (m,3).

Workup

  1. customThe cooling bath is removed
  2. customThe benzene is removed under reduced pressure
  3. customprovides a residue which
  4. washwashed with saturated ammonium chloride
  5. concentrationThe ether layer is concentrated under reduced pressure

Sources & evidence

ORD record
ord-4f4f202b0c7649758da42a8dec41db76
Source dataset
uspto-grants-1993_09
Patent number
US05248830

Reaction notes

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