3,9-Dimethylpentacene-5,7(12H,14H)-dione → HCID 22269468, compound

HRID 983754Notes

Reaction equation

HRID 983754 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:20]([C:21](=O)[C:22]=2[CH:23]=1)=[CH:19][C:18]1[C:17](=O)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:26])[CH:15]=2)[CH2:10][C:9]=1[CH:8]=3>COCCOCCOC>[CH3:26][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][C:18]3[C:9]([CH:10]=2)=[CH:8][C:7]2[C:20](=[CH:21][C:22]4[C:5]([CH:6]=2)=[CH:4][CH:3]=[C:2]([CH3:1])[CH:23]=4)[CH:19]=3)[CH:15]=1

Participants

3

Reactant 1

HCID 222694733,9-Dimethylpentacene-5,7(12H,14H)-dione

Product 1

HCID 22269468HCID 22269468, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1 gram of 3,9-dimethylpentacene-5,7(12H,14H)-dione and 10 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 0.948 grams of sodium borohydride and stirring was continued at room temperature overnight. To the mixture was added 6.3 mL of methanol and stirring was continued for 1.5 hours at room temperature. To the mixture was added 15 mL of acetic acid and 10 mL of concentrated hydrochloric acid. The mixture was stirred for one hour at room temperature followed by heating for one hour at 60° C. To the mixture was added 50 mL of water and the solid was isolated by filtration and washed with water. The solid was washed with tetrahydrofuran until a pale filtrate resulted. The resulting solid was washed with heptane and dried under an atmosphere of nitrogen to give 2,10-dimethylpentacene.

Workup

  1. customflushed with nitrogen for 15 minutes
  2. additionTo this was added 0.948 grams of sodium borohydride
  3. stirringstirring
  4. additionTo the mixture was added 6.3 mL of methanol
  5. stirringstirring
  6. waitwas continued for 1.5 hours at room temperature
  7. additionTo the mixture was added 15 mL of acetic acid and 10 mL of concentrated hydrochloric acid
  8. stirringThe mixture was stirred for one hour at room temperature
  9. additionTo the mixture was added 50 mL of water
  10. customthe solid was isolated by filtration
  11. washwashed with water
  12. washThe solid was washed with tetrahydrofuran until a pale filtrate
  13. customresulted
  14. washThe resulting solid was washed with heptane
  15. customdried under an atmosphere of nitrogen

Sources & evidence

ORD record
ord-19c7fa9c9f1240f290c9a6ffbff5f726
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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