Water → HCID 14116044, compound

HRID 374545Notes

Reaction equation

HRID 374545 reaction equation
[CH:1]1[C:17]2[C:16]3[C:8](=[C:9]4[C:13](=[CH:14][CH:15]=3)[CH2:12][CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.O.ClC1C(=O)C(C#N)=C(C#N)C(=[O:27])C=1Cl>C(O)(=O)C.CCOCC>[CH:1]1[C:17]2[C:16]3[C:8](=[C:9]4[C:13](=[CH:14][CH:15]=3)[C:12](=[O:27])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14116041HCID 14116041, compound

Product 1

HCID 14116044HCID 14116044, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

The hydrocarbon (5) 48 mg; 0.22 mmol) was dissolved in hot acetic acid (15 ml) and water (5 ml) was added slowly with stirring to maintain homogeneity of the solution. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (198 mg, 0.88 mmol) was added, changing the color of the solution to dark green. Stirring was continued at reflux for 30 min. during which time the color of the solution changed to dark red. The reaction mixture was cooled and diluted with ether, and the ether layer was washed with water and aqueous NaOH. The solution was dried over MgSO4 and evaporated to provide a white solid which was chromatographed on a column of Florisil™. Elution with ether yielded 6 (39 mg, 76%):m.p. 127°-128° C.; NMR δ272 (t,1,H15 or 16), 2.85-2.91 (m,4,H6,7), 3.07 (t,1,H15 or 16), 7.24-7.31 (m,3,H2,3,4), 7.67-7.77 (m,3,H1,11,12). Anal. Calc'd. for C17H14O: C,87.25; H,6.02. Found: C,87.13; H,6.03.

Workup

  1. temperatureto maintain homogeneity of the solution
  2. stirringStirring
  3. temperatureat reflux for 30 min. during which time the color of the solution
  4. temperatureThe reaction mixture was cooled
  5. washthe ether layer was washed with water and aqueous NaOH
  6. dry with materialThe solution was dried over MgSO4
  7. customevaporated
  8. customto provide a white solid which
  9. customwas chromatographed on a column of Florisil™
  10. washElution with ether

Sources & evidence

ORD record
ord-d69da1715ef84b578fead0f2b3b94e35
Source dataset
uspto-grants-1996_01
Patent number
US05480913

Reaction notes

Loading…