Potassium Phosphate, Dibasic → 2-(4-Fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-epoxycyclohexane

HRID 6518

Reaction equation

HRID 6518 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH:20]=2)=[CH:15][C:14]=1[CH3:29].OP([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]23[O:9][CH:20]2[C:21]([CH3:28])([CH3:27])[CH2:22][C:23]([CH3:25])([CH3:26])[CH2:24]3)=[CH:15][C:14]=1[CH3:29]

Participants

5

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 70297m-Chloroperbenzoic acidHCID 27693514'-Fluoro-3,3,3',5,5-pentamethyl-2,3,4,5-tetrahydro-1,1'-biphenyl

Product 1

HCID 539343032-(4-Fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-epoxycyclohexaneYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of meta-chloroperbenzoic acid (20 g, 90 mmol) in 250 ml of CH2Cl2 is added dropwise to a cooled (0° C.) solution of 1-fluoro-2-methyl-4-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)benzene (15 g, 61 mmol) and K2HPO4 (21 g, 90 mmol) in dry CH2Cl2 (100 ml). The resulting milky solution is stirred at room temperature for 14 hours, filtered and washed successively with 5% cold NaOH (2×50 ml), H2O (2×50 ml) and brine (75 ml). The CH2Cl2 fraction is dried (MgSO4), and the solvent is removed under reduced pressure to provide 14 g (88%) of 2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-epoxycyclohexane: 1H NMR δ=0.9 (s,6), 0.95 (s,3), 1.1 (s,3), 1.15 (q,2), 1.85 (AB-q, 2), 2.1 (s,3), 2.55 (s,1), 6.85 (t,1), 7.1 (t,1), 7.25 (dd,1).

Workup

  1. filtrationfiltered
  2. washwashed successively with 5% cold NaOH (2×50 ml), H2O (2×50 ml) and brine (75 ml)
  3. dry with materialThe CH2Cl2 fraction is dried (MgSO4)
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-6f275656c8da41b3801c8b460fc918fa
Source dataset
uspto-grants-1993_09
Patent number
US05248830

Linked notes

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