Sodium Carbonate → HCID 14685115, compound

HRID 248786Notes

Reaction equation

HRID 248786 reaction equation
[O:1]1[CH:3]2[CH:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:5][CH2:6][CH:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:2]12.C([O-])([O-])=[O:21].[Na+].[Na+].[K+].[Br-]>CC(C)=O>[C:14]1([CH:4]2[CH2:5][CH2:6][CH:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:2]([OH:21])[CH:3]2[OH:1])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 253877Potassium BromideHCID 14685114HCID 14685114, compound

Product 1

HCID 14685115HCID 14685115, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,2-Epoxy-3,6-diphenylcyclohexane (32 mg, 0.13 mmol) was dissolved in acetone (10 mL). HClO4 (6%, 10 mL) was added and the mixture was stirred at room temperature for 24 hours. The reaction solution was neutralized with Na2CO3 and the reaction mixture was reduced to approximately half volume under reduced pressure. Extraction with CH2Cl2 and removal of the solvent yielded crude product (93% yield) as a white solid. Based upon the analyses of NMR spectra of crude and recrystallized product, reaction gave a single product. Recrystallization from hexane/CH2Cl2 gave pure product as a white crystalline solid: mp 134°-135° C.; IR (KBr) 3303, 3086, 3059, 3026, 2935, 2858, 1603, 1495, 1454, 1041, 760, 698 cm-1 ; 1H NMR (200 MHz, CDCl3) δ 7.20-7.60 (m, 10 H), 4.08 (t, J=9.8 Hz, 1 H), 3.95 (dd, J= 9.5, 5.5 Hz, 1 H), 3.56 (m, 1 H), 2.67 (ddd, J=11.7, 9.9, 4.3 Hz, 1 H), 1.65-2.39 (m, 6 H); 13C NMR (50 MHz, CDCl3) δ 142.3, 140.8, 129.7, 128.8, 128.4, 127.8, 126.9, 126.5, 76.8, 74.6, 50.6, 44.7, 29.9, 29.2; MS (EI) m/e (relative intensity) 268 (M+, 61.9), 250 (12.9), 237 (11.5), 219 (7.3), 146 (30.1), 131 (94.9), 117 55.4), 104 (100.0), 91 (73.6), 77 (15.3); HRMS calcd. for C18H20O2 m/e 268.1463, found m/e 268.1464.

Workup

  1. extractionExtraction
  2. customwith CH2Cl2 and removal of the solvent
  3. customyielded crude product (93% yield) as a white solid
  4. customrecrystallized
  5. customproduct, reaction
  6. customgave a single product
  7. customRecrystallization from hexane/CH2Cl2
  8. customgave pure product as a white crystalline solid

Sources & evidence

ORD record
ord-d61c921fe8394b68bbbbbfb140fc2fd6
Source dataset
uspto-grants-1993_05
Patent number
US05211889

Reaction notes

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