HCID 86757260, compound → HCID 86757259, compound

HRID 651210Notes

Reaction equation

HRID 651210 reaction equation
[CH:1]1[C:14]2=[C:15]3[C:16]4[C:11]([CH:12]=[CH:13]2)=[C:10]2[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=[CH:8][C:7]=4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.C([O:23][C:24](=[O:29])[CH2:25][CH2:26][CH:27]=[O:28])C>O1CCOCC1.Cl>[CH:1]1[C:14]2=[C:15]3[C:16]4[C:11]([CH:12]=[CH:13]2)=[C:10]2[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=[CH:8][C:7]=4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[O:28]=[CH:27][CH2:26][CH2:25][C:24]([OH:29])=[O:23]

Participants

4

Reactant 1

HCID 86757260HCID 86757260, compound2×

Product 1

HCID 86757259HCID 86757259, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Next, benzo[a]pyrene-4-oxobutyric acid (compound 2b) was synthesized from compound 1b. Compound 1b (890 mg; 2.3 mmol) was dissolved in a mixture of dioxane (5 ml) and 2.4 N aqueous hydrochloric acid (5 ml), and the mixture was stirred for 6 hours under reflux with heating. The reaction mixture was extracted with dichloromethane, the organic layer was washed with water, and the solvent was then removed under a reduced pressure. The residue was washed with dichloromethane to obtain 555 mg (67% yield) of compound 2b as a position-isomer mixture.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. extractionThe reaction mixture was extracted with dichloromethane
  4. washthe organic layer was washed with water
  5. customthe solvent was then removed under a reduced pressure
  6. washThe residue was washed with dichloromethane

Sources & evidence

ORD record
ord-1a82f9a6078a4907a8e6ef0c5eefa132
Source dataset
uspto-grants-2001_08
Patent number
US06277964B1

Reaction notes

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