Hexane → HCID 86213022, compound

HRID 347605Notes

Reaction equation

HRID 347605 reaction equation
[CH3:1][O:2][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.[CH3:15][O:16][C:17]([C:19]#[C:20][C:21]([O:23][CH3:24])=[O:22])=[O:18].CCCCCC.CCOC(C)=O>[N+](C1C=CC=CC=1)([O-])=O>[CH3:15][O:16][C:17]([C:19]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:13]=[C:6]2[C:5]=1[CH:4]=[C:3]([O:2][CH3:1])[C:12]1[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:18]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 12980Dimethyl acetylenedicarboxylateHCID 220567321-Ethenyl-4-methoxynaphthalene

Product 1

HCID 86213022HCID 86213022, compoundYield 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-9d186c56330844cb8b8f1f8d912bc6a3
Source dataset
uspto-grants-2007_02
Patent number
US07175958B2

Reaction notes

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