Methylhydroquinone → 1-Heptadecene

HRID 1595133Notes

Reaction equation

HRID 1595133 reaction equation
[CH3:1][CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C[C:14]1[CH:20]=[C:19](O)C=[CH:17][C:15]=1O>CO>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:17][CH2:15][CH2:14][CH2:20][CH3:19]

Participants

4

Reactant 2

HCID 7253MethylhydroquinoneHCID 1372853-Dodecen2×

Product 1

HCID 232171-Heptadecene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-methoxycarboniltetracyclo [4.4.0.12,5.117,10]-3-dodecen of 65 grams, dicyclopentadien of 87 grams and methylhydroquinon of 0.14 gram were mixed in a 300 milli-litter eggplant type flask, and the reaction was continued at 170 degrees to 180 degrees in centigrade for 17 hours. The reaction product remained cooled, and residual 8-methoxycarboniltetracyclo [4.4.0.12,5.117,10]-3-dodecen and residual dicyclopentadien were distillated in vacuum. Hot methanol was added to the residue, and insoluble content was filtrated. The filtrate was concentrated in vacuum, and residue was recrystallized from methanol. Then, we obtained white crystal of 12-methoxycarbonilhexacyclo [6.6.1.13,6.110,13.02,7.09,14] heptadecen of 10 grams.

Workup

  1. temperatureThe reaction product remained cooled
  2. filtrationwas filtrated
  3. concentrationThe filtrate was concentrated in vacuum, and residue
  4. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-d3f25a8a1156417d98aff3ba9262b8d2
Source dataset
uspto-grants-2001_09
Patent number
US06287746B1

Reaction notes

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