HCID 22269454, compound → 2,9-Dinonylpentacene

HRID 983729Notes

Reaction equation

HRID 983729 reaction equation
[CH2:1]([C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][C:15]3[C:28]([C:29](=O)[C:30]=2[CH:31]=1)=[CH:27][C:26]1[CH2:25][C:24]2[C:19](=[CH:20][C:21]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:22][CH:23]=2)[C:18](=O)[C:17]=1[CH:16]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>COCCOCCOC>[CH2:33]([C:21]1[CH:22]=[CH:23][C:24]2[C:19](=[CH:18][C:17]3[C:26]([CH:25]=2)=[CH:27][C:28]2[C:15](=[CH:14][C:13]4[C:30]([CH:29]=2)=[CH:31][C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:11][CH:12]=4)[CH:16]=3)[CH:20]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

3

Reactant 1

HCID 22269454HCID 22269454, compound

Product 1

HCID 222694512,9-Dinonylpentacene

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A mixture of 20 grams of 7,14-dihydro-3,10-dinonylpentacene-5,12-dione and 400 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 11.4 grams of sodium borohydride and stirring was continued at 60° C. for 18 hours. The resulting mixture was cooled to room temperature, 3.0 grams of sodium borohydride was added, and stirring was continued for 16 hours at room temperature. To the resulting mixture was added 170 mL of acetic acid, and the mixture was heated at 60° C. for one hour. To this mixture was added 120 mL of concentrated hydrochloric acid and heating was continued at 60° C. for one hour. The resulting mixture was cooled to room temperature and the solid was collected by filtration and dried to give 2,9-dinonylpentacene.

Workup

  1. customflushed with nitrogen for 15 minutes
  2. additionTo this was added 11.4 grams of sodium borohydride
  3. stirringstirring
  4. addition3.0 grams of sodium borohydride was added
  5. stirringstirring
  6. waitwas continued for 16 hours at room temperature
  7. additionTo the resulting mixture was added 170 mL of acetic acid
  8. temperaturethe mixture was heated at 60° C. for one hour
  9. additionTo this mixture was added 120 mL of concentrated hydrochloric acid
  10. temperatureheating
  11. waitwas continued at 60° C. for one hour
  12. temperatureThe resulting mixture was cooled to room temperature
  13. filtrationthe solid was collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-1b280bc06a224a1bb311e80acac35c6c
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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