7,14-Dihydro-1,4,8,11-tetramethylpentacene-5,12-dione → 1,4,8,11-Tetramethylpentacene

HRID 488968Notes

Reaction equation

HRID 488968 reaction equation
[CH3:1][C:2]1[C:23]2[CH2:22][C:21]3[C:8](=[CH:9][C:10]4[CH2:11][C:12]5[C:17]([C:18](=O)[C:19]=4[CH:20]=3)=[C:16]([CH3:25])[CH:15]=[CH:14][C:13]=5[CH3:26])[C:7](=O)[C:6]=2[C:5]([CH3:28])=[CH:4][CH:3]=1>COCCOCCOC>[CH3:28][C:5]1[C:6]2[C:23](=[CH:22][C:21]3[C:8]([CH:7]=2)=[CH:9][C:10]2[C:19](=[CH:18][C:17]4[C:12]([CH:11]=2)=[C:13]([CH3:26])[CH:14]=[CH:15][C:16]=4[CH3:25])[CH:20]=3)[C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

3

Reactant 1

HCID 222694677,14-Dihydro-1,4,8,11-tetramethylpentacene-5,12-dione

Product 1

HCID 179733711,4,8,11-Tetramethylpentacene

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.0 grams of 7,14-dihydro-1,4,8,11-tetramethylpentacene-5,12-dione and 10 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 0.875 grams of sodium borohydride and stirring was continued at room temperature overnight. To the mixture was added 20 mL of 2-methoxyethyl ether and 0.75 grams of sodium borohydride and heating was continued overnight at 60° C. To the mixture was added 6.3 mL of methanol and 0.75 grams of sodium borohydride and stirring was continued for 6 hours at room temperature. To the mixture was added 15 mL of acetic acid and the mixture was stirred for one hour at room temperature. To the mixture was added 10 mL of concentrated hydrochloric acid and the mixture was heated to 60° C. for 1.5 hours. The solid was isolated by filtration, washed with water and dried to give 1,4,8,11-tetramethylpentacene.

Workup

  1. customflushed with nitrogen for 15 minutes
  2. additionTo this was added 0.875 grams of sodium borohydride
  3. stirringstirring
  4. additionTo the mixture was added 20 mL of 2-methoxyethyl ether and 0.75 grams of sodium borohydride
  5. temperatureheating
  6. waitwas continued overnight at 60° C
  7. additionTo the mixture was added 6.3 mL of methanol and 0.75 grams of sodium borohydride
  8. stirringstirring
  9. waitwas continued for 6 hours at room temperature
  10. additionTo the mixture was added 15 mL of acetic acid
  11. stirringthe mixture was stirred for one hour at room temperature
  12. additionTo the mixture was added 10 mL of concentrated hydrochloric acid
  13. customThe solid was isolated by filtration
  14. washwashed with water
  15. customdried

Sources & evidence

ORD record
ord-fa15d63e7cc74720be0f80b221fae87f
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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