2,2,4-Trimethylpentane → Naphthalene

HRID 1657183Notes

Reaction equation

HRID 1657183 reaction equation
[N+]([C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[CH:9]=[CH:10][C:11](N=C=O)=[CH:12][C:13]=3[CH2:14]2)=[CH:6][CH:5]=1)([O-])=O.[CH:20](CC(C)(C)C)(C)C>>[C:7]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:4]=[CH:5][CH:6]=1.[CH:16]1[C:15]2[CH:20]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH:11]1[CH:10]=[CH:9][C:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[CH:16][C:15]=3[CH2:14][CH2:20][C:13]=2[CH:12]=1.[CH:9]1[C:8]2[C:13](=[CH:14][CH:15]=[CH:16][CH:4]=2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 109072,2,4-TrimethylpentaneHCID 19787217HCID 19787217, compound

Product 4

HCID 931NaphthaleneHCID 995PhenanthreneHCID 7095BiphenylHCID 130589,10-Dihydrophenanthrene

Procedure

In a flask fitted with an air-cooled condenser was added 2-amino-7-nitrofluorene (2.26 grams), ethylene dichloride (25.0 grams) and trichloromethylchloroformate (1.98 grams). The reaction mixture was heated on a steam bath for about 16 hours before the hot mixture was filtered and the solids washed with ethylene dichloride (25 grams). To the combined filtrate was added hot isooctane (50 grams) and the resulting solution allowed to cool to room temperature. The crystals were filtered off, washed with isooctane, and dried at 100° C. to produce 0.98 gram of a yellow solid, m.p. 198°-200° C. A second crop of solid was obtained by evaporation of the filtrate down to 20 mL and the addition of isooctane (100 mL). This solid was digested at 80° C. for 1 hour before it was filtered off and washed with additional isooctane to give 1.38 grams, m.p. 188°-192° C. A total yield of 2.36 grams (93%) was obtained. This product, 7-nitro-2-fluorenylisocyanate, contained some yellow infusible solids, but was still useable. In similar fashion was made 4'-nitrostilbene-4-isocyanate, having m.p. 170° C. (98% yield). These nonlineaphores are preferred on the basis of theoretical calculations, μβ being larger for these than for 4'-nitrobiphenyl-4-isocyanate. The corresponding nitroisocyanates of biphenyl, phenanthrene, dihydrophenanthrene, and naphthalene are synthesized similarly.

Workup

  1. customA second crop of solid was obtained by evaporation of the filtrate down to 20 mL
  2. filtrationwas filtered off
  3. washwashed with additional isooctane
  4. customto give 1.38 grams, m.p. 188°-192° C
  5. customA total yield of 2.36 grams (93%) was obtained

Sources & evidence

ORD record
ord-5d8c13b4b790447c8c488c54e023cb53
Source dataset
uspto-grants-1993_10
Patent number
US05256784

Reaction notes

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