Sodium Bicarbonate → Phenanthrene

HRID 22630

Reaction equation

HRID 22630 reaction equation
COC([C:5]1[C:6](C(OC)=O)=[CH:7][CH:8]=[C:9]2[C:18]=1[CH:17]=[C:16](OC)[C:15]1[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=1)=O.[Na+].C(=O)([O-])O>O>[CH:5]1[C:18]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86213022HCID 86213022, compound

Product 1

HCID 995PhenanthreneYield 131.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9-methoxy phenanthrene-1,2-dicarboxylic acid dimethyl ester 8.11 g (0.025 mol) obtained in the example I-1 was dissolved in chloride methylene 100 ml, by ice-cooling and mixing under nitrogen gas airstreams, 1M 3 bromide boron/chloride methylene solution 100 ml (0.1 mol) was dropped for 60 minutes, and further a mixing reaction was performed for 5 hours under a room temperature. Then, reactants were poured into an ice, water was added, and further hydrogen carbonate sodium 8.4 g (0.1 mol) was added and mixed sufficiently, accordingly extracted crystals were filtered. Then, they were washed twice by 500 ml ion exchange water and dried under reduced pressure at the temperature of 60° C., thus 5.84 g (yield 88.4%) objective phenanthrene compound was obtained. An infrared absorption spectrum of this phenanthrene compound is shown in FIG. 5.

Workup

  1. temperaturecooling
  2. additionwas dropped for 60 minutes
  3. customfurther a mixing reaction
  4. additionwas added
  5. additionmixed sufficiently
  6. filtrationaccordingly extracted crystals were filtered
  7. washThen, they were washed twice by 500 ml ion exchange water
  8. customdried under reduced pressure at the temperature of 60° C.

Sources & evidence

ORD record
ord-75883c4ec9424922860bf1a567fe62c6
Source dataset
uspto-grants-2005_02
Patent number
US06849367B2

Linked notes

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