HCID 22269449, compound → 2,9-Didodecylpentacene

HRID 488961Notes

Reaction equation

HRID 488961 reaction equation
[CH2:1]([C:13]1[CH:14]=[CH:15][C:16]2[CH2:17][C:18]3[C:31]([C:32](=O)[C:33]=2[CH:34]=1)=[CH:30][C:29]1[CH2:28][C:27]2[C:22](=[CH:23][C:24]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:25][CH:26]=2)[C:21](=O)[C:20]=1[CH:19]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>COCCOCCOC>[CH2:36]([C:24]1[CH:25]=[CH:26][C:27]2[C:22](=[CH:21][C:20]3[C:29]([CH:28]=2)=[CH:30][C:31]2[C:18](=[CH:17][C:16]4[C:33]([CH:32]=2)=[CH:34][C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][CH:15]=4)[CH:19]=3)[CH:23]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

3

Reactant 1

HCID 22269449HCID 22269449, compound

Product 1

HCID 222694802,9-Didodecylpentacene

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8.5 grams of 3,10-didodecyl-7,14-dihydropentacene-5,12-dione and 250 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 4.46 grams of sodium borohydride. The resulting mixture was heated to 60° C. for 18 hours. The mixture was cooled to room temperature, and 42 mL of methanol was added slowly. The resulting mixture was stirred at room temperature for 30 minutes. To this was added 1.2 grams of sodium borohydride, and stirring was continued at room temperature for 16 hours. To the resulting mixture was added 60 mL of acetic acid, and the mixture was heated at 60° C. for one hour. To this mixture was added 43 mL of concentrated hydrochloric acid, and heating was continued at 60° C. for one hour. To the resulting mixture was added 100 mL of water and the mixture cooled to room temperature and the solid was collected by filtration and dried to give 2,9-didodecylpentacene.

Workup

  1. customflushed with nitrogen for 15 minutes
  2. additionTo this was added 4.46 grams of sodium borohydride
  3. temperatureThe mixture was cooled to room temperature
  4. addition42 mL of methanol was added slowly
  5. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  6. additionTo this was added 1.2 grams of sodium borohydride
  7. stirringstirring
  8. additionTo the resulting mixture was added 60 mL of acetic acid
  9. temperaturethe mixture was heated at 60° C. for one hour
  10. additionTo this mixture was added 43 mL of concentrated hydrochloric acid
  11. temperatureheating
  12. waitwas continued at 60° C. for one hour
  13. additionTo the resulting mixture was added 100 mL of water
  14. temperaturethe mixture cooled to room temperature
  15. filtrationthe solid was collected by filtration
  16. customdried

Sources & evidence

ORD record
ord-b685f23776ec44aa85b1d7163b06e100
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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