Hexane → Phenanthrene

HRID 22629

Reaction equation

HRID 22629 reaction equation
CO[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[CH2:14])=[CH:5][CH:4]=1.CO[C:17]([C:19]#CC(OC)=O)=O.CCCCCC.CCOC(C)=O>[N+](C1C=CC=CC=1)([O-])=O>[CH:11]1[C:12]2[CH:3]=[CH:4][C:5]3[C:6](=[CH:13][CH:14]=[CH:17][CH:19]=3)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 12980Dimethyl acetylenedicarboxylateHCID 22056732HCID 22056732, compound

Product 1

HCID 995PhenanthreneYield 61.2%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

1-methoxy-4-vinyl naphthalene 18.42 g (0.1 mol) and acetylene dicarboxylic acid dimethyl ester 28.42 g (0.2 mol) were dissolved in nitrobenzene, 200 ml, and they were reacted for 7 hours at the temperature of 130° C. After cooling, nitrobenzene was escaped in vapor under a reduced pressure condition, silica gel column chromatography (developing solvent n-hexane: an acetic acid ethyl=9:1) process was performed to residual elements, crude material, 23.08 g, was obtained. Further, objective phenanthrene compounds, 19.85 g (yield 61.2%) was obtained by recrystallizing from n-butanol. A melting point was 150.2 to 151.0° C. An infrared absorption spectrum of this phenanthrene compound is shown in FIG. 4.

Workup

  1. custom200 ml, and they were reacted for 7 hours at the temperature of 130° C
  2. temperatureAfter cooling
  3. customwas obtained

Sources & evidence

ORD record
ord-966873ba36774f7eb74c09b8155b13af
Source dataset
uspto-grants-2005_02
Patent number
US06849367B2

Linked notes

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