Potassium Carbonate → HCID 14685114, compound

HRID 1769926Notes

Reaction equation

HRID 1769926 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:27])C=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[O:27]1[CH:11]2[CH:10]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:12]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 14685109HCID 14685109, compound

Product 1

HCID 14685114HCID 14685114, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,6-Diphenylcyclohex-1-ene (50 mg, 0.21 mmol), m-chloroperbenzoic acid (55%, 200 mg, 0.64 mmol), and K2CO3 (150 mg, 1.09 mmol) were stirred in CH2Cl2 (10 mL) for 24 hours. The reaction mixture was filtered and washed with CH2Cl2 (40 mL). The filtrate and aqueous Na2S2O3 solution (10%, 10 mL) were stirred for 2 hours. The organic phase was washed with saturated NaHCO3 solution and H2O and dried over anhydrous magnesium sulfate. Preparative thin-layer chromatography (silica gel, 2 mm, developed with 10:1 hexane/EtOAc) gave 1,2-epoxy-3,6-diphenylcyclohexane (32 mg, 60% yield) as a colorless oil along with recovery of starting material (10 mg, 20%). 1,2-Epoxy-3,6-diphenylcyclohexane: 1H NMR (200 MHz, CDCl3) δ 7.20-7.45 (m, 10 H), 3.45 (s, 2 H), 3.37 (t, J=6.4 Hz, 2 H), 1.67-1.88 (m, 2 H), 1.37-1.58 (m, 2 H); 13C NMR (50 MHz), 143.2, 128.6, 128.0, 126.5, 56.2, 39.9, 25.0.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with CH2Cl2 (40 mL)
  3. washThe organic phase was washed with saturated NaHCO3 solution and H2O
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-7fc6f35137174aeb8d2575407df432f7
Source dataset
uspto-grants-1995_01
Patent number
US05384078

Reaction notes

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